Plan a trip to see Bailiwick Repertory Theatre

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The Peninsula Chicago

Downtown Chicago

Save 100% on your flight

per person

23 Sept - 26 Sept

found 24 hours ago

Return flight included

London (LHR) to Chicago (ORD)

9.8/10 Exceptional! (1,000 reviews)

Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

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per person

22 Oct - 29 Oct

found 16 hours ago

Return direct flight included

London (LHR) to Chicago (ORD)

9.2/10 Wonderful! (270 reviews)

walkable to many desireable places.

Reviewed on 16 Jul 2025

Arlo Chicago

Downtown Chicago

per person

22 Oct - 29 Oct

found 16 hours ago

Return direct flight included

London (LHR) to Chicago (ORD)

9.2/10 Wonderful! (1,809 reviews)

A great boutique property in the heart of old town Chicago! Close to parks, transportation, and many dining and entertainment options.

Reviewed on 5 Aug 2025

Tours & day trips

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Architecture River Tour

Free cancellation available

Food, drink & nightlife

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Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

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Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

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Catch an event at Wrigley View Rooftop during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Stage 773

You can get tickets for a performance at Stage 773 during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

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You can get tickets for a performance at Theater Wit during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

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Athenaeum Theatre

You can enjoy a show at Athenaeum Theatre during your stay in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.