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Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

per person

30 May - 2 Jun

found 9 hours ago

Return flight included

Toronto (YYZ) to Chicago (ORD)

9/10 Wonderful! (295 reviews)

Game room was a hit!

Reviewed on 26 Mar 2025

The Emily Hotel

Downtown Chicago

Save 100% on your flight

per person

30 May - 2 Jun

found 9 hours ago

Return flight included

Toronto (YYZ) to Chicago (ORD)

9/10 Wonderful! (1,046 reviews)

The Emily Hotel is a phenomenal place. Leo at the front desk was amazing at checking us in and making our experience so much better. Great stay!! And we look forward to going back for rooftop movie nights!!!

Reviewed on 23 Mar 2025

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

30 May - 2 Jun

found 9 hours ago

Return flight included

Toronto (YYZ) to Chicago (ORD)

8/10 Very Good! (1,524 reviews)

Love booking a room there

Reviewed on 23 Mar 2025

Tours & day trips

See all 142 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 30 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 29 activities

Chicago Favourites Ultimate Food and Walking Tour

Free cancellation available

Attractions

See all 20 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 13 activities

Shooting + Spinning Private Art Experience

Free cancellation available

Popular places to visit

Clarke House Museum

You can spend time studying the exhibits at Clarke House Museum during your travels in Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

Glessner House Museum

You can spend time exploring the galleries in Glessner House Museum during your trip to Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

South Wentworth Street

You can find the perfect gifts to bring home at South Wentworth Street during your trip to Chicago. Amble around this family-friendly area's Chinatown and enjoy its top-notch restaurants.

Ping Tom Memorial Park

After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Chess Records Building / Blues Heaven

You can spend time exploring the galleries in Chess Records Building / Blues Heaven during your trip to Chicago. While in this vibrant area, you can savour the top-notch restaurants.