Title: Pleasant Home in Chicago - Tours and Activities | Expedia.ca

  

[Pleasant Home Hotels](https://expedia.ca/Pleasant-Home-Hotels.0-l553248621532658640-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Pleasant Home Car Rentals](https://expedia.ca/Car-Rentals-In-Pleasant-Home.d553248621532658640.Car-Rental-Guide)[Chicago Vacation Packages](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides)

# Pleasant Home Tours and Activities

## Visit Pleasant Home

Activities

[Chicago travel guide](https://expedia.ca/Chicago.dx178248)

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## Plan a trip to see Pleasant Home

Price found within the past 48 hours. Click for updated prices.

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $725

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=hEcxEAl0cQr8TKY7Kq7rzn7uRX57nVi-PuD3D-VQ8MI5khn6yJn9_A97exaWzUtT)

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $971

per person

Dec 12 - Dec 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=qgNx3gK80nWwTZhFUtG94Km3NC-12tv5tJ5gG4HtEuvfY_egNRgtMbjxkCB3mgj9)

![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Orrington / Evanston

Downtown Evanston

CA $739

per person

Dec 6 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

7.6/10 Good! (1,003 reviews)

The location of the Orrington is excellent but the star of the Orrington is delfinitely its staff. They were friendly, helpful and handled busy and problem situations with grace and solutions. Gotta love the midwest!

Reviewed on Oct 10, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-06/2025-12-13/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19722&paandie=true&dealMarker=3N3YfoFxJicbUeztIgTC6uuv3gFfXqj8V21r6w91FhojRebiAQq6bhgJKWmWxHSJ)

### Tours & day trips

[See all 155 activities](https://expedia.ca/things-to-do/search?&rid=553248621532658640&location=Pleasant+Home&filter.categories=ToursDayTrips)

![Architecture River Tour](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=resizecrop&rw=500&rh=280)

### Architecture River Tour

1h 15m

9.6/10

1,489 reviews

Free cancellation available

CA $68

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=resizecrop&rw=500&rh=280)

### Wendella's 90-min Chicago River Architecture Tour

1h 30m

9.4/10

348 reviews

CA $63

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago By Night River & Lake Cruise](https://mediaim.expedia.com/localexpert/3025324/61ed97b0-d1b6-48bf-864d-4262ada314be.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago By Night River & Lake Cruise

1h 30m

9.6/10

22 reviews

CA $63

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-by-night-river-lake-cruise.a3025324.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago Hop-On Hop-Off Big Bus Tour](https://mediaim.expedia.com/localexpert/370132/082d94cf-cd61-4eef-bd73-4ae89827446f.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Hop-On Hop-Off Big Bus Tour

1d+

8.4/10

528 reviews

Free cancellation available

CA $63CA $57

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-hop-on-hop-off-big-bus-tour.a370132.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago: Navy Pier Centennial Wheel Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Navy Pier Centennial Wheel Ticket

15m

8.4/10

70 reviews

Free cancellation available

CA $34

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago Architecture Centre River Cruise aboard First Lady](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Architecture Centre River Cruise aboard First Lady

1h 30m

9.6/10

77 reviews

CA $78

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-architecture-centre-river-cruise-aboard-chicagos-first-lady.a46106377.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago Sightseeing River and Lake Cruise](https://mediaim.expedia.com/localexpert/3025326/78e3976d-797f-4538-b4af-1e6872d837dd.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Sightseeing River and Lake Cruise

1h 30m

9.8/10

19 reviews

Free cancellation available

CA $63

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-urban-adventure-river-and-lake-cruise.a3025326.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago: Architecture Boat Tour with Drinks](https://mediaim.expedia.com/localexpert/48360649/efaa1a37-df53-4ed1-b5a8-ea2d6a80fef3.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Architecture Boat Tour with Drinks

1h 30m

9/10

20 reviews

Free cancellation available

CA $59

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-architecture-boat-tour-with-drinks.a48360649.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Wendella's Lake and River Architecture Tour](https://mediaim.expedia.com/localexpert/766210/243b3b6c-3da3-47e5-b0c3-a50a9169e092.jpg?impolicy=resizecrop&rw=500&rh=280)

### Wendella's Lake and River Architecture Tour

1h 30m

9.4/10

101 reviews

CA $63

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/wendellas-lake-and-river-architecture-tour.a766210.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago Creepy Cruise](https://mediaim.expedia.com/localexpert/48800785/683758af-ae68-4539-9e8e-7ebf30b3c96a.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Creepy Cruise

1h 30m

6.6/10

7 reviews

Free cancellation available

CA $63

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-creepy-cruise.a48800785.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

### Private & custom tours

[See all 35 activities](https://expedia.ca/things-to-do/search?&rid=553248621532658640&location=Pleasant+Home&filter.categories=Privatecustomtours)

![Eastside Chicago The Heist Exploration Game and Tour](https://mediaim.expedia.com/localexpert/3890294/81b5e167-e685-4d58-838c-285ff8f59b36.jpg?impolicy=resizecrop&rw=500&rh=280)

### Eastside Chicago The Heist Exploration Game and Tour

1h 35m

Free cancellation available

CA $13

includes taxes & fees

per adult\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/chicago-quest-experience-the-heist.a3890294.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Gangster Story Quest Experience in Chicago](https://mediaim.expedia.com/localexpert/46532851/ec65726f-ec55-421d-a106-7462f0c68e9e.jpg?impolicy=resizecrop&rw=500&rh=280)

### Gangster Story Quest Experience in Chicago

1h 30m

Free cancellation available

CA $13

includes taxes & fees

per adult\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/gangster-story-quest-experience-in-chicago.a46532851.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Dragon Kings Quest Experience in Chinatown Chicago](https://mediaim.expedia.com/localexpert/45763663/10042599-8522-494c-9792-d0fd1c2d7541.jpg?impolicy=resizecrop&rw=500&rh=280)

### Dragon Kings Quest Experience in Chinatown Chicago

1h 18m

Free cancellation available

CA $12

includes taxes & fees

per adult\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/chicago-chinatown-search-for-the-dragon-kings-exploration-game.a45763663.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago's Dark Side Self-Guided Smartphone Walking Tour](https://mediaim.expedia.com/localexpert/45050109/ef12e622-b3cc-423d-8c42-bff85382c663.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago's Dark Side Self-Guided Smartphone Walking Tour

1h 15m

9.8/10

6 reviews

Free cancellation available

CA $14

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicagos-dark-side-self-guided-smartphone-walking-tour.a45050109.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago Helicopter 25-Mile Tour for up to Three Passengers](https://mediaim.expedia.com/localexpert/49372529/b4180bc6-eaea-4b45-9bcc-293144eaa526.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Helicopter 25-Mile Tour for up to Three Passengers

15m

Free cancellation available

CA $909

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/the-chicago-helicopter-tour-25-miles-up-to-3-passengers.a49372529.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago Lincoln Square Quest Experience](https://mediaim.expedia.com/localexpert/46447859/d9bc96c4-54a6-40e0-8300-2fc9b8d98bf7.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Lincoln Square Quest Experience

2h 20m

10/10

1 review

Free cancellation available

CA $15

includes taxes & fees

per adult\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/chicago-lincoln-square-city-exploration-game.a46447859.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Haunted Chicago Exploration Game and Tour](https://mediaim.expedia.com/localexpert/4887774/df42f142-ff19-4d48-9cee-05b481517e79.jpg?impolicy=resizecrop&rw=500&rh=280)

### Haunted Chicago Exploration Game and Tour

2h

Free cancellation available

CA $13

includes taxes & fees

per adult\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/ghosts-of-chicago-haunted-city-exploration-game.a4887774.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Luxury SUV 4-Hours Sightseeing Tour in Chicago DT Hourly Service](https://mediaim.expedia.com/localexpert/48720490/c794b857-dd2d-4158-af8e-fc3d79b4d5c5.jpg?impolicy=resizecrop&rw=500&rh=280)

### Luxury SUV 4-Hours Sightseeing Tour in Chicago DT Hourly Service

4h

Free cancellation available

CA $490

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/luxury-suv-4-hours-sightseeing-tour-in-chicago-dt-hourly-service.a48720490.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![️ Chicago Instagram Walking Tour (Private & All- Inclusive)](https://mediaim.expedia.com/localexpert/3525296/8222a6f5-a101-4494-8e22-de36ce12b1ad.jpg?impolicy=resizecrop&rw=500&rh=280)

### ️ Chicago Instagram Walking Tour (Private & All- Inclusive)

4h

Free cancellation available

CA $330

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-instagram-walking-tour-private-all-inclusive.a3525296.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Private Chicago Fire TV Show Set Tour](https://mediaim.expedia.com/localexpert/48957697/aa6e6cb1-bf1f-4c1c-9f2e-1e4dde8c39ff.jpg?impolicy=resizecrop&rw=500&rh=280)

### Private Chicago Fire TV Show Set Tour

2h

Free cancellation available

CA $441

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/northwestern-university-or-loyola-university-scenic-driving-tour.a48957697.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

### Food, drink & nightlife

[See all 23 activities](https://expedia.ca/things-to-do/search?&rid=553248621532658640&location=Pleasant+Home&filter.categories=FoodDrinkNightlife)

![Chicago: Architecture Boat Tour with Drinks](https://mediaim.expedia.com/localexpert/48360649/efaa1a37-df53-4ed1-b5a8-ea2d6a80fef3.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Architecture Boat Tour with Drinks

1h 30m

9/10

20 reviews

Free cancellation available

CA $59

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-architecture-boat-tour-with-drinks.a48360649.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago Craft Brewery Barrel Bus Tour](https://mediaim.expedia.com/localexpert/2135529/ed799f6f-aa8b-4c85-8c30-a268559b812c.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Craft Brewery Barrel Bus Tour

3h 45m

10/10

9 reviews

Free cancellation available

CA $139

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-craft-brewery-barrel-bus-tour.a2135529.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago: Secret Food Tour](https://mediaim.expedia.com/localexpert/4518775/969d4bd1-f30f-4057-a555-7cb8451b6d6e.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Secret Food Tour

3h

10/10

2 reviews

Free cancellation available

CA $129

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-secret-food-tour.a4518775.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Private, Self-Guided Deep Dish Pizza Foodie Tour](https://mediaim.expedia.com/localexpert/4017194/c8bb95e9-5b12-47af-8e02-3331c3655ec2.jpg?impolicy=resizecrop&rw=500&rh=280)

### Private, Self-Guided Deep Dish Pizza Foodie Tour

2h

CA $104

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/private-self-guided-deep-dish-pizza-foodie-tour.a4017194.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago: City centre Donut Tour with Tastings](https://mediaim.expedia.com/localexpert/4520600/07198f80-6895-45cd-9961-cba02a1e43aa.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: City centre Donut Tour with Tastings

2h

9.4/10

6 reviews

Free cancellation available

CA $95

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-city-centre-donut-tour-with-tastings.a4520600.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Odyssey Chicago River Premier Dinner Cruise](https://mediaim.expedia.com/localexpert/551583/255ce58f-49a5-4ac8-8116-bddf0ba1a738.jpg?impolicy=resizecrop&rw=500&rh=280)

### Odyssey Chicago River Premier Dinner Cruise

2h 30m

7.4/10

3 reviews

CA $342

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/odyssey-chicago-river-premier-dinner-cruise.a551583.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago: Prohibition Speakeasies Bus Tour or Walking Tour](https://mediaim.expedia.com/localexpert/45730860/75853642-30c8-45d5-89f5-76f6f534e0ad.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

3h+

10/10

4 reviews

Free cancellation available

CA $67

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-prohibition-speakeasies-bus-tour-or-walking-tour.a45730860.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Vito's Vault Chicago finest dinner theatre speakeasy](https://mediaim.expedia.com/localexpert/50395749/d17809ab-2475-4929-9b8d-777b231a5fc3.jpg?impolicy=resizecrop&rw=500&rh=280)

### Vito's Vault Chicago finest dinner theatre speakeasy

3h

6/10

1 review

Free cancellation available

CA $119

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/vitos-vault-chicago-finest-dinner-theatre-speakeasy.a50395749.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Bites & History: Chicago Small Group Food Tour](https://mediaim.expedia.com/localexpert/643295/6378865a-ab16-429f-bd38-5a78df600d9b.jpg?impolicy=resizecrop&rw=500&rh=280)

### Bites & History: Chicago Small Group Food Tour

2h

Free cancellation available

CA $105

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/historic-chicago-small-group-food-tour-with-a-local-guide.a643295.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago: Tapas & Flamenco Dinner in Ukrainian Village](https://mediaim.expedia.com/localexpert/48202094/ae8e99e3-cc76-452d-81c1-af521d534677.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Tapas & Flamenco Dinner in Ukrainian Village

2h

Free cancellation available

CA $235

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-tapas-flamenco-dinner-in-ukrainian-village.a48202094.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

### Attractions

[See all 14 activities](https://expedia.ca/things-to-do/search?&rid=553248621532658640&location=Pleasant+Home&filter.categories=Attractions)

![360 CHICAGO Observation Deck](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=resizecrop&rw=500&rh=280)

### 360 CHICAGO Observation Deck

30m+

8.4/10

672 reviews

Free cancellation available

CA $41

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago CityPASS®: Experience 5 must-see attractions](https://mediaim.expedia.com/localexpert/190061/f189c545-768d-4511-ba47-df30303ea656.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago CityPASS®: Experience 5 must-see attractions

9d

9.2/10

784 reviews

Free cancellation available

CA $199

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-citypass-experience-5-must-see-attractions.a190061.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Skydeck Chicago Admission Ticket](https://mediaim.expedia.com/localexpert/1342523/d7dbfa90-2431-442d-b5ad-18eaa98ab71d.jpg?impolicy=resizecrop&rw=500&rh=280)

### Skydeck Chicago Admission Ticket

1h 30m

9.8/10

10 reviews

Free cancellation available

CA $62

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/skydeck-chicago-admission-ticket.a1342523.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago Explorer Pass: Save up to 50 Percent - Includes SkyDeck](https://mediaim.expedia.com/localexpert/259056/50cfbadf-c4d7-49b2-b430-982e46c25417.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Explorer Pass: Save up to 50 Percent - Includes SkyDeck

60d

8/10

474 reviews

Free cancellation available

CA $118

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-explorer-pass-save-up-to-50-percent-includes-skydeck.a259056.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago C3® by CityPASS®](https://mediaim.expedia.com/localexpert/46362450/da44d619-18fc-4969-97e2-f7b8d0da99b5.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago C3® by CityPASS®

9d

8.4/10

28 reviews

Free cancellation available

CA $148

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-c3-by-citypass.a46362450.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Colour Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=resizecrop&rw=500&rh=280)

### Colour Factory Chicago Ticket

1h 30m

9.4/10

3 reviews

CA $48

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/colour-factory-chicago-ticket.a49191714.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Art Institute of Chicago](https://mediaim.expedia.com/localexpert/170360/cfa59fea-c028-46b9-93be-ea78b723f52e.jpg?impolicy=resizecrop&rw=500&rh=280)

### Art Institute of Chicago

9.2/10

167 reviews

Free cancellation available

CA $56

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/art-institute-of-chicago.a170360.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/0b36f3b1-b375-4fa2-8cfd-1a9815dcdcdc.jpg?impolicy=resizecrop&rw=500&rh=280)

### Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting

1h 30m

9.6/10

4 reviews

Free cancellation available

CA $50

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/medieval-torture-museum-ticket-with-audio-guide-and-ghost-hunting.a4973725.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Skip the Line: Public Tour-Adult Admission Ticket (50 mins)](https://mediaim.expedia.com/localexpert/2305131/80825fbb-e94f-47c1-a66a-38efb3b38535.jpg?impolicy=resizecrop&rw=500&rh=280)

### Skip the Line: Public Tour-Adult Admission Ticket (50 mins)

50m

9/10

2 reviews

Free cancellation available

CA $28

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/skip-the-line-public-tour-adult-admission-ticket-50-mins.a2305131.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Rosemont: Two Flight Indoor Skydiving Experience](https://mediaim.expedia.com/localexpert/2573196/563b98e9-df84-4044-9c7b-299dbe003729.jpg?impolicy=resizecrop&rw=500&rh=280)

### Rosemont: Two Flight Indoor Skydiving Experience

1h

6.6/10

7 reviews

Free cancellation available

CA $135

includes taxes & fees

per traveller

[](https://www.expedia.ca/things-to-do/two-flight-indoor-skydiving-experience.a2573196.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

### Classes & workshops

[See all 10 activities](https://expedia.ca/things-to-do/search?&rid=553248621532658640&location=Pleasant+Home&filter.categories=ClassesWorkshops)

![Chicago Perfume Making Classes on Magnificent Mile](https://mediaim.expedia.com/localexpert/48984388/66d0d1b5-ee07-4a92-912f-c6a1ca077f0b.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Perfume Making Classes on Magnificent Mile

1h 15m

10/10

1 review

Free cancellation available

CA $119

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-perfume-making-classes-on-magnificent-mile.a48984388.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago River Yoga Walk](https://mediaim.expedia.com/localexpert/47941135/e2c77204-79de-4bab-9c2f-96211b00f22b.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago River Yoga Walk

1h 30m

Free cancellation available

CA $69

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-river-yoga-walk.a47941135.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Deep Dish Cooking Class at Pizzeria Uno in Chicago](https://mediaim.expedia.com/localexpert/49021707/386cbc8b-bde1-44e8-86cd-03269cda87ab.jpg?impolicy=resizecrop&rw=500&rh=280)

### Deep Dish Cooking Class at Pizzeria Uno in Chicago

1h 30m

4/10

1 review

Free cancellation available

CA $83

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/deep-dish-cooking-class-at-pizzeria-uno-in-chicago.a49021707.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago Candle Making Class On Magnificent Mile](https://mediaim.expedia.com/localexpert/46062339/1fe61b03-4426-4fdb-bbce-7f66e1a2de44.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Candle Making Class On Magnificent Mile

1h 15m

8/10

1 review

Free cancellation available

CA $105

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/candle-therapy-class.a46062339.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Chicago: Private Catamaran Sailing for up to 12 people](https://mediaim.expedia.com/localexpert/49244960/5dc72281-64f5-4e3d-963b-58bdc23012d5.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Private Catamaran Sailing for up to 12 people

2h+

Free cancellation available

CA $2,098

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/chicago-private-catamaran-sailing-for-up-to-12-people.a49244960.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Private Bear Painting Class in Chicago](https://mediaim.expedia.com/localexpert/48687236/924933c4-9eed-40b3-a8d2-e9b65623f55d.jpg?impolicy=resizecrop&rw=500&rh=280)

### Private Bear Painting Class in Chicago

45m

CA $130

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/private-fluid-baby-bear-painting.a48687236.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Artisan Italian Pasta Class in Chicago (Includes 3-Course Meal)](https://mediaim.expedia.com/localexpert/50038914/8544de92-83af-402a-bce4-36f5eff534fe.jpg?impolicy=resizecrop&rw=500&rh=280)

### Artisan Italian Pasta Class in Chicago (Includes 3-Course Meal)

2h 30m

Free cancellation available

CA $175

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/artisan-italian-pasta-class-in-chicago-includes-3-course-meal.a50038914.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Pasta Making Cooking Class at a Local Distillery in Chicago](https://mediaim.expedia.com/localexpert/47007807/2f41b2e0-d244-448d-82ac-96f507d1d0fc.jpg?impolicy=resizecrop&rw=500&rh=280)

### Pasta Making Cooking Class at a Local Distillery in Chicago

2h

Free cancellation available

CA $105

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/pasta-making-in-chicago.a47007807.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Private Shooting and Spinning DIY Painting Class in Chicago](https://mediaim.expedia.com/localexpert/47139386/830b069a-05e3-4679-a9ce-ac7bc43ba689.jpg?impolicy=resizecrop&rw=500&rh=280)

### Private Shooting and Spinning DIY Painting Class in Chicago

45m

CA $138

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/private-shooting-and-spinning-diy-painting-class-in-chicago.a47139386.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

![Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)](https://mediaim.expedia.com/localexpert/50038753/3b9cf30c-7dc5-483f-aad9-24f75c78c41b.jpg?impolicy=resizecrop&rw=500&rh=280)

### Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)

2h

Free cancellation available

CA $175

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/exclusive-sushi-making-class-in-chicago-includes-3-course-meal.a50038753.activity-details?&rid=553248621532658640&location=Pleasant+Home&swp=off)

### Popular places to visit

![Unity Temple featuring religious aspects, a temple or place of worship and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26633-Unity-Temple.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Unity Temple

This was Frank Lloyd Wright’s first major public building and is still considered one of his greatest achievements.

[](https://expedia.ca/Unity-Temple-Chicago.d6064079.Vacation-Attraction)

![Ernest Hemingway Museum and House featuring interior views and food](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26697-The-Ernest-Hemingway-Museum-And-House.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Ernest Hemingway Museum and House

Peek into the early life of one America’s best-loved writers.

[](https://expedia.ca/Ernest-Hemingway-Museum-And-House-Chicago.d6241604.Vacation-Attraction)

![Frank Lloyd Wright Historic District](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26555-Frank-Lloyd-Wright-Historic-District.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Frank Lloyd Wright Historic District

Visit the birthplace of modern architecture to explore the world's largest collections of homes and buildings designed by Frank Lloyd Wright.

[](https://expedia.ca/Frank-Lloyd-Wright-Historic-District-Chicago.d553248634340947645.Vacation-Attraction)

#### Mills Park

Mills Park is just one of the places to see in Oak Park, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

[](https://expedia.ca/Mills-Park-Chicago.d553248621532658641.Vacation-Attraction)

#### Oak Park Visitors Center

After visiting Oak Park Visitors Center, make a plan to see the other sights and activities in Oak Park. Discover the top-notch restaurants and acclaimed art scene in this vibrant area.

[](https://expedia.ca/Oak-Park-Visitors-Center-Chicago.d553248621561882957.Vacation-Attraction)

#### Madison Street Theatre

You can make plans for a show at Madison Street Theatre during your trip to Oak Park. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.

[](https://expedia.ca/Madison-Street-Theatre-Chicago.d6247290.Vacation-Attraction)

* * *

## Best Lodging Options Near Pleasant Home

## Check availability on hotels close to Pleasant Home

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=2025-10-24&endDate=2025-10-25)

[Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=2025-10-24&endDate=2025-10-25)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=2025-10-24&endDate=2025-10-25)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=2025-10-24&endDate=2025-10-25)[Oct 24 - Oct 25](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=2025-10-24&endDate=2025-10-25)

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[Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=2025-10-25&endDate=2025-10-26)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=2025-10-25&endDate=2025-10-26)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=2025-10-25&endDate=2025-10-26)[Oct 25 - Oct 26](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=2025-10-25&endDate=2025-10-26)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025)

[This weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025)[Oct 24 - Oct 26](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=553248621532658640&startDate=24%2F10%2F2025&endDate=26%2F10%2F2025)

![Carleton of Oak Park](https://images.trvl-media.com/lodging/1000000/10000/9200/9186/c3e40006_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Carleton of Oak Park

1110 Pleasant St, Oak Park, IL

[](https://expedia.ca/Chicago-Hotels-Carleton-Of-Oak-Park.h9186.Hotel-Information)

![Harvey House Bed & Breakfast](https://images.trvl-media.com/lodging/7000000/6360000/6356600/6356562/b288c54a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Harvey House Bed & Breakfast

107 South Scoville Avenue, Oak Park, IL

[](https://expedia.ca/Chicago-Hotels-Harvey-House-Bed-Breakfast.h6356562.Hotel-Information)

![At Home in Oak Park](https://images.trvl-media.com/lodging/76000000/75610000/75609600/75609586/2e2b5c00_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

At Home in Oak Park

411 N Oak Park Avenue, Oak Park, IL

[](https://expedia.ca/Chicago-Hotels-Home-In-Oak-Park.h75609586.Hotel-Information)

![Historic Oak Park Home](https://images.trvl-media.com/lodging/89000000/88180000/88173500/88173402/7547fb3d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Historic Oak Park Home

421 N Oak Park Avenue, Oak Park, IL

[](https://expedia.ca/Chicago-Hotels-Historic-Oak-Park-Home.h88173402.Hotel-Information)

![Historic Oak Park Residence](https://images.trvl-media.com/lodging/95000000/94680000/94670100/94670079/3a1a2525_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Historic Oak Park Residence

421 N Oak Park Avenue, Oak Park, IL

[](https://expedia.ca/Chicago-Hotels-Historic-Oak-Park-Residence.h94670079.Hotel-Information)

![Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed](https://images.trvl-media.com/lodging/118000000/117680000/117672000/117671933/e376d974_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood

[](https://expedia.ca/Chicago-Hotels-Charming-2-Bedroom-House-In-Maywood-With-WiFi.h117671933.Hotel-Information)

![Experience Chicago living near United Center ](https://images.trvl-media.com/lodging/84000000/83460000/83455900/83455869/57ada61d_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Experience Chicago living near United Center

Chicago

[](https://expedia.ca/Chicago-Hotels-Clean-Cozy-Entire-3-Bedroom-Unit-7-Miles-From-Downtown.h83455869.Hotel-Information)

![Experience Chicago living near
United Center](https://images.trvl-media.com/lodging/88000000/87690000/87684800/87684787/0afb39d6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Experience Chicago living near United Center

Chicago

[](https://expedia.ca/Chicago-Hotels-Experience-Chicago-Living-NearUnited-Center.h87684787.Hotel-Information)

![Travel Inn](https://images.trvl-media.com/lodging/22000000/21520000/21514800/21514796/11ba844f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Travel Inn

1150 Roosevelt Rd, Broadview, IL

[](https://expedia.ca/Chicago-Hotels-Travel-Inn.h21514796.Hotel-Information)

[See all 4,279 properties in Pleasant Home](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=553248621532658640)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.