Plan a trip to see Flat Iron Building

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

Level Chicago – Old Town

Downtown Chicago

CA $650

per person

Oct 17 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Québec (YQB) to Chicago (ORD)

9/10 Wonderful! (347 reviews)

Pool area was great

Reviewed on Sep. 4, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $877

per person

Nov 7 - Nov 11

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (286 reviews)

The staff were excellent

Reviewed on Aug. 21, 2025

The Langham, Chicago

Downtown Chicago

CA $1,377

per person

Oct 23 - Oct 26

found 21 hours ago

Roundtrip flight included

Québec (YQB) to Chicago (ORD)

9.8/10 Exceptional! (1,005 reviews)

Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug. 12, 2025

Tours & day trips

See all 166 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 32 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 31 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Armitage Avenue

During your trip to Chicago, you can do some window-shopping at Armitage Avenue. Stroll along the lakeside in this vibrant area, or check out its lively bars.

Wood Street Gallery

You can spend time exploring the galleries in Wood Street Gallery during your travels in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

AMITA Health Saints Mary and Elizabeth Medical Center Chicago - Saint Elizabeth Campus

Though AMITA Health Saints Mary and Elizabeth Medical Center Chicago - Saint Elizabeth Campus might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here.

Presence Saint Elizabeth Hospital

Though Presence Saint Elizabeth Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here.

Monique Meloche Gallery

You can spend time browsing the exhibits at Monique Meloche Gallery during your travels in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

AMITA Health Saints Mary and Elizabeth Medical Center

Though AMITA Health Saints Mary and Elizabeth Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here.