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

  

[Oak Street Beach Hotels](https://expedia.ca/Oak-Street-Beach-Hotels.0-l6226577-0.Travel-Guide-Filter-Hotels)[Oak Street Beach Car Rentals](https://expedia.ca/Car-Rentals-In-Oak-Street-Beach.d6226577.Car-Rental-Guide)[Downtown Chicago Vacations](https://expedia.ca/Downtown-Chicago.d6350699.Destination-Travel-Guides)

# Oak Street Beach Tours and Activities

![Oak Street Beach](https://mediaim.expedia.com/destination/1/09a13f9a1fc2a6e320d9cf7537bed232.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Photo by Amy Heinen](https://mediaim.expedia.com/destination/2/ac65e3b420bce7cf18bb1622dc30f4ea.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

[Photo by Amy Heinen](https://mediaim.expedia.com/destination/2/ac65e3b420bce7cf18bb1622dc30f4ea.jpg)

![Photo by Roquita Williams](https://mediaim.expedia.com/destination/2/e412e8d33ff03b18ec26f02cb90737a6.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

[Photo by Roquita Williams](https://mediaim.expedia.com/destination/2/e412e8d33ff03b18ec26f02cb90737a6.jpg)

## Visit Oak Street Beach

Activities

* * *

* * *

## Plan a trip to see Oak Street Beach

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

![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Westin Michigan Avenue Chicago

Downtown Chicago

CA $964

per person

Dec 23 - Dec 28

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (1,046 reviews)

One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-28/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=VmzHMI7V6TGtEURhW0Q75qs-Hr_gsGxtxCpI4H5BZ8ywK40CWFySyMaOVi20hTrz)

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $2,313

per person

Nov 28 - Dec 5

found 9 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Excellent all around

Reviewed on Oct 4, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-05/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=BZYqulMtaXoEYsUn3v1k3f56bgy_KCCx3119aPoNbaTHzEPIvlqdxTmaAHb81hJI)

![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 $1,476

per person

Nov 28 - Dec 5

found 9 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.2/10 Wonderful! (1,222 reviews)

Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.

Reviewed on Sep 29, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-28/2025-12-05/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=cfNoKr8a-ai3jLqdMZDFjihVAAmlG-N2JpWXoObfYkVk1p8OrJ3JkOiETf57ln2W)

### Tours & day trips

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### Architecture River Tour

1h 15m

9.6/10

1,479 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=6226577&location=Oak+Street+Beach&swp=off)

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

1h 30m

9.4/10

341 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=6226577&location=Oak+Street+Beach&swp=off)

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### Chicago By Night River & Lake Cruise

1h 30m

9.6/10

21 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=6226577&location=Oak+Street+Beach&swp=off)

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1d+

8.4/10

524 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=6226577&location=Oak+Street+Beach&swp=off)

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### Flyover in Chicago

30m

10/10

5 reviews

Free cancellation available

CA $53

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

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15m

8.4/10

67 reviews

Free cancellation available

CA $34

includes taxes & fees

per adult

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1h 30m

9/10

19 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=6226577&location=Oak+Street+Beach&swp=off)

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1h 30m

10/10

16 reviews

Free cancellation available

CA $63

includes taxes & fees

per adult

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1h 30m

6/10

6 reviews

Free cancellation available

CA $63

includes taxes & fees

per adult

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### Chicago Architecture Centre River Cruise aboard First Lady

1h 30m

9.6/10

74 reviews

CA $78

includes taxes & fees

per adult

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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=6226577&location=Oak+Street+Beach&swp=off)

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### 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=6226577&location=Oak+Street+Beach&swp=off)

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### 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=6226577&location=Oak+Street+Beach&swp=off)

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### 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=6226577&location=Oak+Street+Beach&swp=off)

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### 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=6226577&location=Oak+Street+Beach&swp=off)

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

15m

Free cancellation available

CA $907

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=6226577&location=Oak+Street+Beach&swp=off)

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### 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=6226577&location=Oak+Street+Beach&swp=off)

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

4h

Free cancellation available

CA $329

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-instagram-walking-tour-private-all-inclusive.a3525296.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

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### Private Shameless TV Show Location Tour

2h

Free cancellation available

CA $439

includes taxes & fees

per traveller\*

\*Get lower prices by selecting more than 2 adults

[](https://www.expedia.ca/things-to-do/private-shameless-tv-show-location-tour.a50321504.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

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

4h

Free cancellation available

CA $488

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=6226577&location=Oak+Street+Beach&swp=off)

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1h 30m

9/10

19 reviews

Free cancellation available

CA $59

includes taxes & fees

per adult

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2h 30m

7.6/10

41 reviews

CA $246

includes taxes & fees

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3h 45m

10/10

9 reviews

Free cancellation available

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includes taxes & fees

per adult

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### Chicago: Secret Food Tour

3h

10/10

2 reviews

Free cancellation available

CA $130

includes taxes & fees

per adult

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2h

9.4/10

6 reviews

Free cancellation available

CA $95

includes taxes & fees

per adult

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3h

10/10

4 reviews

Free cancellation available

CA $67

includes taxes & fees

per adult

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3h

6/10

1 review

Free cancellation available

CA $119

includes taxes & fees

per adult

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2h

Free cancellation available

CA $105

includes taxes & fees

per adult

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2h

CA $103

includes taxes & fees

per adult

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2h

Free cancellation available

CA $237

includes taxes & fees

per adult

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9d

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Free cancellation available

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9d

8.4/10

28 reviews

Free cancellation available

CA $148

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### Skydeck Chicago Admission Ticket

1h 30m

10/10

8 reviews

Free cancellation available

CA $61

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/skydeck-chicago-admission-ticket.a1342523.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Colour Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=resizecrop&rw=500&rh=280)

### Colour Factory Chicago Ticket

1h 30m

9.4/10

3 reviews

CA $47

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/colour-factory-chicago-ticket.a49191714.activity-details?&rid=6226577&location=Oak+Street+Beach&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

164 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=6226577&location=Oak+Street+Beach&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=6226577&location=Oak+Street+Beach&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=6226577&location=Oak+Street+Beach&swp=off)

![Chicago's Navy Pier Centennial Wheel Ticket](https://mediaim.expedia.com/localexpert/48840807/8856f18f-7399-4c59-bffa-336edc781f23.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago's Navy Pier Centennial Wheel Ticket

15m

6/10

1 review

Free cancellation available

CA $34

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicagos-navy-pier-centennial-wheel-ticket.a48840807.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

### Adventure & outdoor

[See all 13 activities](https://expedia.ca/things-to-do/search?&rid=6226577&location=Oak+Street+Beach&filter.categories=AdventureOutdoor)

![Chicago: Two Flight Indoor Skydiving Experience](https://mediaim.expedia.com/localexpert/2577742/4234ac6e-21fa-481a-9de6-ed98da9888dd.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago: Two Flight Indoor Skydiving Experience

1h

10/10

1 review

Free cancellation available

CA $143

includes taxes & fees

per traveller

[](https://www.expedia.ca/things-to-do/two-flight-indoor-skydiving-experience.a2577742.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Chicago Full Day Bike Rental](https://mediaim.expedia.com/localexpert/637010/cbd278ac-0281-4492-a3bd-2877e3a09d3f.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Full Day Bike Rental

1d

6/10

2 reviews

Free cancellation available

CA $42

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-full-day-bike-rental.a637010.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Chicago Lakefront Electric Bike Tour](https://mediaim.expedia.com/localexpert/1247101/e914eb05-c7ae-48a2-9622-608fcba27cd1.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Lakefront Electric Bike Tour

1h

Free cancellation available

CA $97

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-lakefront-electric-bike-tour.a1247101.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Chicago's Ultimate City Bike Tour](https://mediaim.expedia.com/localexpert/1342807/1e662383-a2f0-4213-a63e-59b4c1e3fbfb.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago's Ultimate City Bike Tour

3h

10/10

1 review

Free cancellation available

CA $82

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicagos-ultimate-city-bike-tour.a1342807.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Bikes, Brews & Hidden Bars: A Ride Through RiNo & City centre](https://mediaim.expedia.com/localexpert/48577988/3902aba5-fc8e-4942-b144-4a2c92656ede.jpg?impolicy=resizecrop&rw=500&rh=280)

### Bikes, Brews & Hidden Bars: A Ride Through RiNo & City centre

2h 30m

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/bike-and-booze-tour-of-river-north-art-district-city-centre.a48577988.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Chicago's West Side Foodie Ride Bike Tour](https://mediaim.expedia.com/localexpert/2185100/58bf6229-92c8-44e7-aef1-81497c04f5c0.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago's West Side Foodie Ride Bike Tour

4h

10/10

2 reviews

Free cancellation available

CA $138

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicagos-west-side-foodie-ride-bike-tour.a2185100.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer](https://mediaim.expedia.com/localexpert/46208669/1a9520fd-9797-4b2f-b013-aa63087b81e8.jpg?impolicy=resizecrop&rw=500&rh=280)

### Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

4h

Free cancellation available

CA $250

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/fun-chicago-bike-tour-with-pizza-hot-dogs-cupcakes-and-beer.a46208669.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Chicago Family Food and Bike Tour with Top Attractions](https://mediaim.expedia.com/localexpert/2364615/7b8e575c-e42c-40d1-9bd4-616d9b6bd588.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Family Food and Bike Tour with Top Attractions

4h

10/10

2 reviews

Free cancellation available

CA $110

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-family-food-bike-tour-with-top-attractions.a2364615.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Bike Tour of Chicago's Lakefront Areas](https://mediaim.expedia.com/localexpert/2364621/633af1f0-5c2e-43ce-b8a7-c218bfb43e7d.jpg?impolicy=resizecrop&rw=500&rh=280)

### Bike Tour of Chicago's Lakefront Areas

3h

10/10

1 review

Free cancellation available

CA $82

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/bike-tour-of-chicagos-lakefront-areas.a2364621.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

![Chicago Highlights Running Tour](https://mediaim.expedia.com/localexpert/46602003/bf56cabb-53d8-48de-ab7c-48f3930f61fb.jpg?impolicy=resizecrop&rw=500&rh=280)

### Chicago Highlights Running Tour

1h 15m

10/10

1 review

Free cancellation available

CA $61

includes taxes & fees

per adult

[](https://www.expedia.ca/things-to-do/chicago-highlights-running-tour.a46602003.activity-details?&rid=6226577&location=Oak+Street+Beach&swp=off)

### Popular places to visit

![900 North Michigan Shops](https://mediaim.expedia.com/destination/2/8b888b50f54ce7e893fbd8ebe2664e6e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 900 North Michigan Shops

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

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

![Oak Street](https://mediaim.expedia.com/destination/2/3d3782e7b2e84824bf9140ebadf71b9d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Oak Street

During your trip to Chicago, you can do some window-shopping at Oak Street. Experience the acclaimed art scene and entertainment choices in this vibrant area.

[](https://expedia.ca/Oak-Street-Chicago.d6199865.Vacation-Attraction)

![John Hancock Center](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/475000/475716-Chicago-City.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### John Hancock Center

You can find out about the history of Chicago with a visit to John Hancock Center. Amble around this vibrant area's lakeside or experience its fascinating museums.

[](https://expedia.ca/John-Hancock-Center-Downtown-Chicago.d6065131.Vacation-Attraction)

![Fourth Presbyterian Church](https://mediaim.expedia.com/destination/2/e7520c1ef46803ede6a4161a3e096f21.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Fourth Presbyterian Church

Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

[](https://expedia.ca/Fourth-Presbyterian-Church-Chicago.d553248621555594919.Vacation-Attraction)

![Water Tower Place](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192047-Water-Tower-Place.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Water Tower Place

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)

![Chicago Water Tower](https://mediaim.expedia.com/destination/9/2db15ca39dad5af3cf1f9dc1e1531ba3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Water Tower

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)

* * *

## Best Lodging Options Near Oak Street Beach

## Check availability on hotels close to Oak Street Beach

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-05&endDate=2025-10-06)

[Tonight](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-05&endDate=2025-10-06)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-05&endDate=2025-10-06)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-05&endDate=2025-10-06)[Oct 5 - Oct 6](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-05&endDate=2025-10-06)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-06&endDate=2025-10-07)

[Tomorrow night](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-06&endDate=2025-10-07)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-06&endDate=2025-10-07)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-06&endDate=2025-10-07)[Oct 6 - Oct 7](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=2025-10-06&endDate=2025-10-07)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025)

[Next weekend](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025)

[](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025)[Oct 10 - Oct 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true&regionId=6226577&startDate=10%2F10%2F2025&endDate=12%2F10%2F2025)

![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)

![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)

![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)

![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)

![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Freehand Chicago

19 East Ohio Street, Chicago, IL

[](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information)

![Warwick Allerton - Chicago](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Warwick Allerton - Chicago

701 North Michigan Avenue, Chicago, IL

[](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information)

![The Chicago Hotel Collection - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/ca00b143_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street, Chicago, IL

[](https://expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information)

![Hilton Garden Inn Chicago Downtown/Magnificent Mile](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Garden Inn Chicago Downtown/Magnificent Mile

10 E Grand Ave, Chicago, IL

[](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.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)

[See all 4,025 properties in Oak Street Beach](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&regionId=6226577)

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.

### Things to do near Oak Street Beach

Oak Street Beach in Chicago offers a variety of activities for visitors, including shopping at nearby boutiques, engaging in sports like beach volleyball, and enjoying a refreshing swim in Lake Michigan. The vibrant atmosphere is complemented by entertainment options such as live music and events, while popular attractions like the scenic waterfront and parks nearby enhance the overall experience. Whether you're looking to relax or stay active, Oak Street Beach has something for everyone.

**Shopping**

At Oak Street Beach, you can shop at [900 North Michigan Shops](https://www.expedia.ca/900-North-Michigan-Shops-Hotels.0-l6199347-0.Travel-Guide-Filter-Hotels), only 483m away, offering a vibrant mix of entertainment and family-friendly vibes. [Chicago Place Mall](https://www.expedia.ca/Chicago-Place-Mall-Hotels.0-l6199336-0.Travel-Guide-Filter-Hotels), 966m distant, has a bustling urban atmosphere. For a broader experience, if you're up for a drive, visit [City Market](https://www.expedia.ca/City-Market-Hotels.0-l797772754713255936-0.Travel-Guide-Filter-Hotels), located 1.6km away, featuring local businesses and city vibes.

**Recreation**

[Wrigley Field](https://www.expedia.ca/Wrigley-Field-Hotels.0-l6034754-0.Travel-Guide-Filter-Hotels), a vibrant sports stadium, offers an energetic atmosphere just 6.4km from Oak Street Beach, perfect for sports enthusiasts. For musical entertainment, the [House of Blues Chicago](https://www.expedia.ca/House-Of-Blues-Chicago-Hotels.0-l6227753-0.Travel-Guide-Filter-Hotels) is a lively venue located 1.6km away, while [Second City](https://www.expedia.ca/Second-City-Hotels.0-l6129887-0.Travel-Guide-Filter-Hotels), a comedic gem 1.4km away, guarantees family-friendly fun.

**Adventure**

Explore the [Salt Creek Trail](https://www.expedia.ca/Salt-Creek-Trail-Hotels.0-l553248621532658620-0.Travel-Guide-Filter-Hotels) for a scenic hike 19.3km from Oak Street Beach, immersing yourself in nature's beauty. For a splash of fun, head to [Rainbow Falls Waterpark](https://www.expedia.ca/Rainbow-Falls-Waterpark-Hotels.0-l6247247-0.Travel-Guide-Filter-Hotels) 33.8km away, where you can enjoy thrilling water slides and family-friendly activities.

**Nightlife**

Experience the vibrant nightlife at Oak Street Beach. Enjoy a show at the [Chicago Theatre](https://www.expedia.ca/Chicago-Theatre-Hotels.0-l6064049-0.Travel-Guide-Filter-Hotels), just 1.6km away, or unwind at [Dave & Buster's](https://www.expedia.ca/Dave-Busters-Hotels.0-l553248621532658508-0.Travel-Guide-Filter-Hotels), half 1.6km away, for drinks and fun. Don't miss the adventure at [Amazing Chicago's Funhouse Maze](https://www.expedia.ca/Amazing-Chicagos-Funhouse-Maze-Hotels.0-l553248621555594814-0.Travel-Guide-Filter-Hotels), a mile from the beach.

*\*Distances are measured in a straight line; actual driving distances may vary depending on the route.*

### Find the best attractions near Oak Street Beach

When visiting Oak Street Beach in Chicago, you'll find an array of attractions, including stunning skyscrapers, scenic urban parks, and engaging art museums. This vibrant area caters to those seeking cultural experiences, family fun, and iconic tourist spots. Don't miss out on exploring nearby highlights like the picturesque Ohio Street Beach, ensuring a well-rounded experience during your stay in the Windy City.

-   **[Navy Pier:](https://www.expedia.ca/Navy-Pier-Hotels.0-l6069215-0.Travel-Guide-Filter-Hotels)** Experience the vibrant atmosphere at Navy Pier, located 1.6km from Oak Street Beach. This iconic jetty offers stunning views of Lake Michigan, delightful dining options, and plenty of entertainment, making it a perfect spot for a leisurely day out.
-   **[Michigan Avenue:](https://www.expedia.ca/Michigan-Avenue-Hotels.0-l6156167-0.Travel-Guide-Filter-Hotels)** Just 1.3km away, Michigan Avenue is known as the Magnificent Mile. This bustling street is lined with upscale shops, restaurants, and cultural attractions, embodying the dynamic city vibe of Chicago.
-   **[Millennium Park:](https://www.expedia.ca/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels)** Located 1.6km from Oak Street Beach, Millennium Park is a beautiful urban park that caters to families and outdoor enthusiasts alike. Enjoy art installations, concerts, and lush green spaces in the heart of the city.

### Best time to go to Oak Street Beach

The best time to visit Oak Street Beach is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

| **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** |
| --- | --- | --- | --- | --- | --- |
| January | 25.7°F (-3.5°C) | Light Rain | Mostly Cloudy | Average | Slightly Low |
| February | 27.0°F (-2.8°C) | Light Rain | Mostly Cloudy | Average | Slightly Low |
| March | 37.0°F (2.8°C) | Light Rain | Mostly Cloudy | Average | Average |
| April | 46.0°F (7.8°C) | Light Rain | Mostly Sunny | Average | Average |
| May | 57.0°F (13.9°C) | Light Rain | Mostly Sunny | Average | Average |
| June | 67.3°F (19.6°C) | Light Rain | Mostly Sunny | High | Slightly High |
| July | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | High | Average |
| August | 73.0°F (22.8°C) | Light Rain | Mostly Sunny | High | Average |
| September | 67.1°F (19.5°C) | Light Rain | Mostly Sunny | Average | Slightly High |
| October | 54.9°F (12.7°C) | Light Rain | Mostly Sunny | Low | Slightly High |
| November | 42.3°F (5.7°C) | Light Rain | Mostly Sunny | Low | Average |
| December | 33.1°F (0.6°C) | Light Rain | Mostly Cloudy | Low | Slightly Low |

### Booking tips and Expedia advantages for Oak Street Beach

To save money on your trip to Oak Street Beach, consider visiting from December to February when accommodation prices drop. Booking a stay on Monday can also help you avoid the higher Saturday rates. Use Expedia to compare prices and consider package deals that combine flights and hotels for better savings. For public transport, explore options like buses or the 'L' train, which are cost-effective ways to get around the city. Lastly, look for free activities along the beach, such as enjoying the scenic views or walking along the shoreline.

-   **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay around Oak Street Beach are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
-   **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay around Oak Street Beach is Monday. The most expensive day to stay around Oak Street Beach is Saturday.
-   **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to refine your preferences, such as budget, desired location, and preferred hotel type. To find the best prices and offers, arrange the price filter from lowest to highest.
-   **Consider bundling your trip:** Consider saving some money by booking an Expedia package that combines your stay at an Oak Street Beach hotel with your flights and activities. It’s a great way to enjoy your trip while keeping your budget in check.