Title: Oak Street in Downtown Chicago - Tours and Activities | Expedia.ca

[Oak Street Hotels](https://expedia.ca/Oak-Street-Hotels.0-l6199865-0.Travel-Guide-Filter-Hotels)[Oak Street Car Rentals](https://expedia.ca/Car-Rentals-In-Oak-Street.d6199865.Car-Rental-Guide)[Downtown Chicago Vacations](https://expedia.ca/Downtown-Chicago.d6350699.Destination-Travel-Guides)

# Oak Street Tours and Activities

![Oak Street](https://images.trvl-media.com/place/829/618e6946-b4e6-4665-b4ff-5b9e0073f98a.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Oak Street](https://images.trvl-media.com/place/829/618e6946-b4e6-4665-b4ff-5b9e0073f98a.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Oak Street

Activities

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## Plan a trip to see Oak Street

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

![Aloft Chicago Downtown River North](https://images.trvl-media.com/lodging/6000000/5470000/5461400/5461400/w4000h2662x0y0-8993d93f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Aloft Chicago Downtown River North

Downtown Chicago

CA $764

per person

Mar 31 - Apr 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,159 reviews)

Staff was great but next to fire station. Beware very noisy if staying city view

Reviewed on Feb 8, 2026

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Emily Hotel

Downtown Chicago

CA $1,160

per person

Apr 14 - Apr 19

found 1 hour ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9.2/10 Wonderful! (1,264 reviews)

Amazing hotel. Always stay here when I make a trip to Chicago.

Reviewed on Feb 10, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $795

per person

Mar 15 - Mar 19

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Room was clean, staff was so polite and kind and very helpful. We took our 3 year old daughter with us and they were kind to her and welcoming! (That means a lot - not all hotels are welcoming to small children.) they made sure to open the doors for us each time we came in with our stroller. We will absolutely be back to the Riu in Chicago! 10/10

Reviewed on Feb 9, 2026

### Tours & day trips

[See all 154 activities](https://expedia.ca/things-to-do/search?&rid=6199865&location=Oak+Street&filter.categories=ToursDayTrips)

![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=resizecrop&rw=500&rh=280)

### Flyover in Chicago

30m

9.8/10

13 verified reviews

Free cancellation available

CA $52

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details?&rid=6199865&location=Oak+Street&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

8.6/10

735 GetYourGuide reviews

Free cancellation available

CA $33

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Big Bus 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)

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

1d+

8.6/10

534 verified reviews

Free cancellation available

~~CA $62~~CA $55

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-hop-on-hop-off-big-bus-tour.a370132.activity-details?&rid=6199865&location=Oak+Street&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

365 verified reviews

CA $61

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago: Griffin Museum of Science and Industry Ticket](https://mediaim.expedia.com/localexpert/48205552/a70236a3-d3a0-4ccc-a8c2-ae14f2a167f9.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Griffin Museum of Science and Industry Ticket

8.6/10

22 GetYourGuide reviews

Free cancellation available

CA $35

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-griffin-museum-of-science-and-industry-ticket.a48205552.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago Crime and Mob Bus Tour](https://mediaim.expedia.com/localexpert/1342522/774cb728-0244-411c-ad5f-e594d00c816f.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Crime and Mob Bus Tour

2h

9/10

1,128 Viator reviews

Free cancellation available

CA $66

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-crime-and-mob-bus-tour.a1342522.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago's Chinatown Food and Walking Tour](https://mediaim.expedia.com/localexpert/637028/6d7803ed-9e8e-43a3-9767-0f3bfd9372ab.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago's Chinatown Food and Walking Tour

3h

10/10

263 Viator reviews

Free cancellation available

CA $108

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicagos-chinatown-food-and-walking-tour.a637028.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago River: 1.5-Hour Guided Architecture Cruise](https://mediaim.expedia.com/localexpert/4575180/37c87b99-f11d-4fe0-8f87-3e8f807e4c0c.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago River: 1.5-Hour Guided Architecture Cruise

1h 30m

9.6/10

2,273 GetYourGuide reviews

Free cancellation available

CA $60

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-river-1-5-hour-guided-architecture-cruise.a4575180.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago Cocktail Adventure Part 1](https://mediaim.expedia.com/localexpert/51093071/2e6216a0-9aa5-4659-a514-c90efaff9820.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Cocktail Adventure Part 1

3h

Free cancellation available

CA $7

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-cocktail-adventure-part-1.a51093071.activity-details?&rid=6199865&location=Oak+Street&swp=off)

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

### City Cruises Chicago: River Premier Dinner Cruise

2h 30m

7.4/10

3 verified reviews

CA $215

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/odyssey-chicago-river-premier-dinner-cruise.a551583.activity-details?&rid=6199865&location=Oak+Street&swp=off)

### Private & custom tours

[See all 58 activities](https://expedia.ca/things-to-do/search?&rid=6199865&location=Oak+Street&filter.categories=Privatecustomtours)

![Chicago Cocktail Adventure Part 1](https://mediaim.expedia.com/localexpert/51093071/2e6216a0-9aa5-4659-a514-c90efaff9820.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Cocktail Adventure Part 1

3h

Free cancellation available

CA $7

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-cocktail-adventure-part-1.a51093071.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Honeymooners Private South Guided Tour Mauritius](https://mediaim.expedia.com/localexpert/50727117/69fd8a7b-119f-47ea-92f9-9312d728b4a5.jpg?impolicy=resizecrop&rw=500&rh=280)

### Honeymooners Private South Guided Tour Mauritius

8h

Free cancellation available

CA $142

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/honeymooners-private-south-guided-tour-mauritius.a50727117.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Experience Chicago Cocktail Adventure Part 2](https://mediaim.expedia.com/localexpert/51012523/da6eb0ed-2347-4866-88f0-bfd46554da5f.jpg?impolicy=resizecrop&rw=500&rh=280)

### Experience Chicago Cocktail Adventure Part 2

3h

Free cancellation available

CA $7

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/experience-chicago-cocktail-adventure-part-2.a51012523.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![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

4/10

2 Viator reviews

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=6199865&location=Oak+Street&swp=off)

![Chamarel 7 Colours and Waterfalls - Exclusive South West Tour](https://mediaim.expedia.com/localexpert/47622470/122339ef-1d06-4bc0-8314-f95a00f6155f.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chamarel 7 Colours and Waterfalls - Exclusive South West Tour

9h

9.8/10

32 Viator reviews

Free cancellation available

CA $170

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/private-chamarel-7-colours-and-waterfalls-south-west-tour.a47622470.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Mauritius South Adventure Crocodile Park Rum Tasting and Lunch](https://mediaim.expedia.com/localexpert/51055464/802ca099-7754-42a8-b25d-c6573b1442e5.jpg?impolicy=resizecrop&rw=500&rh=280)

### Mauritius South Adventure Crocodile Park Rum Tasting and Lunch

8h

Free cancellation available

CA $212

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/mauritius-south-adventure-crocodile-park-rum-tasting-and-lunch.a51055464.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago City Boat Tours](https://mediaim.expedia.com/localexpert/50815182/59d3e0ed-af25-4437-8dac-3b08e2397665.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago City Boat Tours

8h

Free cancellation available

CA $406

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/chicago-city-boat-tours.a50815182.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago Gangsters: Self-Guided Crime Story Puzzle Walk](https://mediaim.expedia.com/localexpert/46532851/ec65726f-ec55-421d-a106-7462f0c68e9e.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Gangsters: Self-Guided Crime Story Puzzle Walk

1h 30m

6/10

2 Viator reviews

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=6199865&location=Oak+Street&swp=off)

![Fascinating Nature Tour Incl Ebony Forest, 7 Coloured Earth,Lunch](https://mediaim.expedia.com/localexpert/46041149/953c47c8-4f6c-4ee5-a6fc-84ed375676d7.jpg?impolicy=resizecrop&rw=500&rh=280)

### Fascinating Nature Tour Incl Ebony Forest, 7 Coloured Earth,Lunch

8h

10/10

2 Viator reviews

Free cancellation available

CA $183

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/fascinating-nature-tour-incl-ebony-forest-7-coloured-earth-lunch.a46041149.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Explore Mauritius South: 7-Coloured Earth, Curious Corner + Lunch](https://mediaim.expedia.com/localexpert/50221316/1862eaeb-e0f1-4269-a9d9-0e2db5248651.jpg?impolicy=resizecrop&rw=500&rh=280)

### Explore Mauritius South: 7-Coloured Earth, Curious Corner + Lunch

8h

Free cancellation available

CA $172

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/explore-mauritius-south-seven-coloured-earth.a50221316.activity-details?&rid=6199865&location=Oak+Street&swp=off)

### Food, drink & nightlife

[See all 24 activities](https://expedia.ca/things-to-do/search?&rid=6199865&location=Oak+Street&filter.categories=FoodDrinkNightlife)

![Chicago's Chinatown Food and Walking Tour](https://mediaim.expedia.com/localexpert/637028/6d7803ed-9e8e-43a3-9767-0f3bfd9372ab.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago's Chinatown Food and Walking Tour

3h

10/10

263 Viator reviews

Free cancellation available

CA $108

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicagos-chinatown-food-and-walking-tour.a637028.activity-details?&rid=6199865&location=Oak+Street&swp=off)

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

### City Cruises Chicago: River Premier Dinner Cruise

2h 30m

7.4/10

3 verified reviews

CA $215

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/odyssey-chicago-river-premier-dinner-cruise.a551583.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago Favourites Ultimate Food and Walking Tour](https://mediaim.expedia.com/localexpert/1342675/c631318d-3b4e-4c4e-96bb-2afa3d0dc20f.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Favourites Ultimate Food and Walking Tour

3h

9.8/10

816 Viator reviews

Free cancellation available

CA $115

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-favourites-ultimate-food-and-walking-tour.a1342675.activity-details?&rid=6199865&location=Oak+Street&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

9.8/10

152 Viator reviews

Free cancellation available

CA $135

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-craft-brewery-barrel-bus-tour.a2135529.activity-details?&rid=6199865&location=Oak+Street&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

8/10

2 verified reviews

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=6199865&location=Oak+Street&swp=off)

![Tea Around Town: Chicago Tea Experience & City Sights](https://mediaim.expedia.com/localexpert/50874193/5cf73a78-bfd7-45cb-9d84-996443148e52.jpg?impolicy=resizecrop&rw=500&rh=280)

### Tea Around Town: Chicago Tea Experience & City Sights

1h 30m

10/10

1 Viator review

CA $107

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/tea-around-town-chicago-tea-experience-city-sights.a50874193.activity-details?&rid=6199865&location=Oak+Street&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 $136

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/private-self-guided-deep-dish-pizza-foodie-tour.a4017194.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour](https://mediaim.expedia.com/localexpert/46449456/86de9933-7149-4319-ae44-dd059b4affb9.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour

1h 30m

10/10

1 Viator review

Free cancellation available

CA $69

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/michelin-spanish-dinner-with-live-flamenco.a46449456.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago: Discover the City's Most Delicious Donuts With Us](https://mediaim.expedia.com/localexpert/4520600/62cadae3-5341-4219-b4ea-9e1c5b993914.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Discover the City's Most Delicious Donuts With Us

2h

9.6/10

64 GetYourGuide reviews

Free cancellation available

CA $92

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-city-centre-donut-tour-with-tastings.a4520600.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago Pizza Tour](https://mediaim.expedia.com/localexpert/1342684/56dad504-072a-4bf7-9ec7-23cbcc76956f.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Pizza Tour

3h 30m

9.8/10

202 Viator reviews

Free cancellation available

CA $121

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-pizza-tour.a1342684.activity-details?&rid=6199865&location=Oak+Street&swp=off)

### Attractions

[See all 19 activities](https://expedia.ca/things-to-do/search?&rid=6199865&location=Oak+Street&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+

8.6/10

699 verified reviews

Free cancellation available

CA $39

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details?&rid=6199865&location=Oak+Street&swp=off)

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

9d

9.4/10

794 verified reviews

Free cancellation available

CA $193

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-citypass-experience-5-must-see-attractions.a190061.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Skydeck - Willis Tower Admission](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=resizecrop&rw=500&rh=280)

### Skydeck - Willis Tower Admission

1h 30m

9.2/10

476 Viator reviews

Free cancellation available

CA $60

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/skydeck-chicago-admission-ticket.a1342523.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago Bulls Basketball Game at United Centre](https://mediaim.expedia.com/localexpert/47300776/972792e4-c31c-4347-9c2d-8d50ffbad913.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Bulls Basketball Game at United Centre

3h

8/10

1 verified review

CA $86

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-bulls-basketball-game-at-united-centre.a47300776.activity-details?&rid=6199865&location=Oak+Street&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

9.6/10

5 verified reviews

CA $46

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/colour-factory-chicago-ticket.a49191714.activity-details?&rid=6199865&location=Oak+Street&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

9/10

32 verified reviews

Free cancellation available

CA $144

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-c3-by-citypass.a46362450.activity-details?&rid=6199865&location=Oak+Street&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

8.4/10

475 verified reviews

Free cancellation available

CA $114

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=6199865&location=Oak+Street&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

181 verified reviews

Free cancellation available

CA $54

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/art-institute-of-chicago.a170360.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/317321c4-e25a-4f59-82c4-45a13dc80967.jpg?impolicy=resizecrop&rw=500&rh=280)

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

1h 30m

9/10

31 Viator reviews

Free cancellation available

CA $49

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=6199865&location=Oak+Street&swp=off)

![Chicago Museum of Contemporary Art: General Admission Ticket](https://mediaim.expedia.com/localexpert/3555286/e03b8a8b-7d7a-4be4-a0d1-c82fae7865cc.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Museum of Contemporary Art: General Admission Ticket

3h

8/10

21 Viator reviews

Free cancellation available

CA $30

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-museum-of-contemporary-art-general-admission-ticket.a3555286.activity-details?&rid=6199865&location=Oak+Street&swp=off)

### Classes & workshops

[See all 13 activities](https://expedia.ca/things-to-do/search?&rid=6199865&location=Oak+Street&filter.categories=ClassesWorkshops)

![BYOB Spray Paint and Sip at Studio W.I.P.](https://mediaim.expedia.com/localexpert/2185446/88b1414b-ad56-47d3-ae19-f8c1710c206d.jpg?impolicy=resizecrop&rw=500&rh=280)

### BYOB Spray Paint and Sip at Studio W.I.P.

1h 30m

9.8/10

235 Viator reviews

Free cancellation available

CA $61

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/byob-spray-paint-n-sip-at-studio-w-i-p-chicago.a2185446.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Neon Paint Therapy Experience](https://mediaim.expedia.com/localexpert/51106756/d2accf14-e251-4bea-a87b-08770019f85e.jpg?impolicy=resizecrop&rw=500&rh=280)

### Neon Paint Therapy Experience

30m

CA $134

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/neon-paint-therapy-experience.a51106756.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![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

9.4/10

10 Viator reviews

Free cancellation available

CA $115

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-perfume-making-classes-on-magnificent-mile.a48984388.activity-details?&rid=6199865&location=Oak+Street&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 $126

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/private-fluid-baby-bear-painting.a48687236.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour](https://mediaim.expedia.com/localexpert/46449456/86de9933-7149-4319-ae44-dd059b4affb9.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour

1h 30m

10/10

1 Viator review

Free cancellation available

CA $69

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/michelin-spanish-dinner-with-live-flamenco.a46449456.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Private Shooting and Spinning DIY Painting Class in Chicago](https://mediaim.expedia.com/localexpert/47139386/bc2b5fb3-4da3-49eb-8683-b69471eb4dd3.jpg?impolicy=resizecrop&rw=500&rh=280)

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

45m

CA $134

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=6199865&location=Oak+Street&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

9/10

14 Viator reviews

Free cancellation available

CA $102

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/candle-therapy-class.a46062339.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Cooking Class with Celebrity Chef Tony Hu](https://mediaim.expedia.com/localexpert/50866226/63099d69-733a-45a3-abee-9376dbcb185c.jpg?impolicy=resizecrop&rw=500&rh=280)

### Cooking Class with Celebrity Chef Tony Hu

1h 30m

Free cancellation available

CA $183

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/cooking-class-with-celebrity-chef-tony-hu.a50866226.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Make Your Own Art: Adults-Only Private Art Experience in Chicago](https://mediaim.expedia.com/localexpert/48687247/a48618f0-78bd-4440-bcd2-2214f76adb65.jpg?impolicy=resizecrop&rw=500&rh=280)

### Make Your Own Art: Adults-Only Private Art Experience in Chicago

1h 30m

Free cancellation available

CA $264

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/adults-party-private-art-shot-in-chicago.a48687247.activity-details?&rid=6199865&location=Oak+Street&swp=off)

![Private Indian-Mexican Fusion Cooking Class with a Modern Cook in Chicago](https://mediaim.expedia.com/localexpert/3516016/2d05d5bc-a143-4aab-8429-bb73aab75f91.jpg?impolicy=resizecrop&rw=500&rh=280)

### Private Indian-Mexican Fusion Cooking Class with a Modern Cook in Chicago

3h

10/10

3 Viator reviews

Free cancellation available

CA $133

includes taxes & fees

per adult\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/private-indian-mexican-fusion-cooking-class-with-a-modern-cook.a3516016.activity-details?&rid=6199865&location=Oak+Street&swp=off)

### Popular places to visit

![At Bloomingdales, great place to shop and eat. 🎄](https://images.trvl-media.com/place/829/90dde0a9-6fb9-4838-b442-4c81b1fba161.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 900 North Michigan Shops

4/5(5 reviews)

You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area. 

[](https://expedia.ca/900-North-Michigan-Shops-Downtown-Chicago.d6199347.Vacation-Attraction)

![John Hancock Center featuring a city, night scenes and landscape views](https://images.trvl-media.com/place/6065131/31560e8f-121e-4823-9cdb-02b104f564cc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 875 North Michigan Avenue

4.5/5(194 reviews)

You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed art scene. 

[](https://expedia.ca/875-North-Michigan-Avenue-Downtown-Chicago.d6065131.Vacation-Attraction)

![Chicago Gold Coast highrise residential towers with a lakeshore beach in the foreground.](https://images.trvl-media.com/place/6130105/d1074c27-6139-40f3-8e96-c39328236bbf.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Oak Street Beach

Why not spend a carefree afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the fascinating museums in this vibrant area. 

[](https://expedia.ca/Oak-Street-Beach-Downtown-Chicago.d6226577.Vacation-Attraction)

![Water Tower view on Michigan Ave in Chicago City](https://images.trvl-media.com/place/6064051/c7da0472-a993-406a-b23d-6dce83229f3a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Water Tower

4/5(82 reviews)

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art scene. 

[](https://expedia.ca/Chicago-Water-Tower-Chicago.d6064051.Vacation-Attraction)

![Water Tower Place](https://images.trvl-media.com/place/6064087/b6a04578-7f57-4437-b0b1-672d4ae44f19.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Water Tower Place

4.5/5(67 reviews)

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

[](https://expedia.ca/Water-Tower-Place-Downtown-Chicago.d6064087.Vacation-Attraction)

![Holy Name cathedral, Chicago](https://images.trvl-media.com/place/829/72fea9c8-342e-4868-a6c9-338188137c30.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Holy Name Cathedral

3.5/5(6 reviews)

After visiting Holy Name Cathedral, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area. 

[](https://expedia.ca/Holy-Name-Cathedral-Chicago.d6246831.Vacation-Attraction)

---

## Best Lodging Options Near Oak Street

## Check availability on hotels close to Oak Street

[Tonight

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6199865&startDate=2026-02-10&endDate=2026-02-11)[Feb 10 - Feb 11](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6199865&startDate=2026-02-10&endDate=2026-02-11)

[Tomorrow night

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6199865&startDate=2026-02-11&endDate=2026-02-12)[Feb 11 - Feb 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6199865&startDate=2026-02-11&endDate=2026-02-12)

[This weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6199865&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6199865&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)

[Next weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6199865&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[Feb 20 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6199865&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

[](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

[](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

[](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information)

![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Aloft Chicago Mag Mile

243 E. Ontario Chicago IL

[](https://expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information)

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

[](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information)

![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Eurostars Magnificent Mile

660 North State Street Chicago IL

[](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information)

![Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/4e2c019f_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

201 East Walton Place Chicago IL

[](https://expedia.ca/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information)

![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Courtyard by Marriott Chicago Magnificent Mile

165 East Ontario Street Chicago IL

[](https://expedia.ca/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information)

![The Whitehall Hotel, BW Premier Collection](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Whitehall Hotel, BW Premier Collection

105 E Delaware Pl Chicago IL

[](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information)

[See all 4,199 properties in Oak Street](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=6199865)

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.