Plan a trip to see Euclid Square Park

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Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

Save 100% on your flight

£1,074

per person

8 Oct - 12 Oct

found 1 day ago

Return direct flight included

London (LON) to Chicago (ORD)

9.4/10 Exceptional! (1,014 reviews)

We loved the experience! We shall come back again😊

Reviewed on 24 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

£1,465

per person

8 Oct - 15 Oct

found 9 hours ago

Return direct flight included

London (LGW) to Chicago (ORD)

9.4/10 Exceptional! (2,087 reviews)

Loved the view from the room of Lake Michigan.

Reviewed on 25 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago

£1,399

per person

8 Oct - 15 Oct

found 9 hours ago

Return direct flight included

London (LGW) to Chicago (ORD)

9/10 Wonderful! (1,962 reviews)

The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Tours & day trips

See all 167 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 36 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 28 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 15 activities

Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

Unity Temple

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

Ernest Hemingway Museum and House

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

Frank Lloyd Wright Historic District

4/5(1 review)

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

Oak Park Conservatory

Enjoy a stop at Oak Park Conservatory, an entertaining place to visit in Oak Park. Amble around this vibrant area's riverfront or experience its acclaimed art galleries.

Madison Street Theatre

You can get tickets for a performance at Madison Street Theatre during your trip to Oak Park. Stroll along the lakeside or experience the entertainment choices in this vibrant area.