Plan a trip to see Lollapalooza

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Arlo Chicago

Downtown Chicago

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per person

Jun. 28 - Jul. 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,665 reviews)

Amazing stay! The views were great, it was located near everything, it was very clean and the bed felt wonderful! I will definitely be going back w

Reviewed on Apr. 15, 2025

Dorothy's

Lakeview

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per person

Jun. 20 - Jun. 25

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

8.4/10 Very Good! (24 reviews)

It was great for a stay in Boystown

Reviewed on Apr. 9, 2025

Level Chicago - River North

Downtown Chicago

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per person

May 15 - May 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (501 reviews)

Another absolutely fabulous stay. Levels always exceed my expectations with their facilities, staff, cleanliness, balconies (love the balcony) and views of the city. Natalie remembers me and greets me with a smile, every time. Best of Chicago!

Reviewed on Apr. 11, 2025

Tours & day trips

See all 150 activities

Flyover in Chicago

Free cancellation available

Food, drink & nightlife

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Chicago Favourites Ultimate Food and Walking Tour

Free cancellation available

Private & custom tours

See all 26 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

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Shooting + Spinning Private Art Experience

Free cancellation available

Popular places to visit

Grant Park

4.5/5(291 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Buckingham Fountain

4.5/5(118 reviews)

This enormous art deco installation gives free regular water and light shows symbolizing the power and might of Lake Michigan.

Gen. John Logan Memorial

Set on a grassy mound in a quiet corner of Grant Park, this equestrian statue celebrates an American Civil War hero and faithful servant of Abraham Lincoln.

Roosevelt University

5/5(1 review)

Explore the campus of Roosevelt University during your stay in Chicago. Experience the acclaimed art scene and entertainment choices in this vibrant area.

Auditorium Building and Theatre

4/5(2 reviews)

You can make plans for a show at Auditorium Building and Theatre during your trip to Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.