Plan a trip to see Lookingglass Theatre

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

The Royal Sonesta Chicago River North

Downtown Chicago

per person

Oct 24 - Oct 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,980 reviews)

so I gotta say The royal sonesta river north in particular is amazing it feels more like a hotel, it feels like a small community and all the staff and guest know each other. The front desk woman Gabby is amazing and dope as heck. Shaunda is a travel guide there, shes hilarious and gave us wonderful recommendations in the area. Antwonne is a dope Bellman great service and attitude. Every detail was perfect Jessenia apart of the housekeeping staff has such good attention to detail when it came to fixing up and cleaning the room everything was so organized and neat. Now to the room it couldn't have been more perfect they upgraded us to the luxury suite and it was beautiful (use the tub as much as you can)

Reviewed on Aug. 15, 2025

Park Hyatt Chicago

Downtown Chicago

per person

Oct 5 - Oct 11

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,000 reviews)

Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on Aug. 10, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

per person

Oct 24 - Oct 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,679 reviews)

One of the best hotels. I will definitely stay here again.

Reviewed on Aug. 16, 2025

Tours & day trips

See all 176 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 33 activities

Chicago's Dark Side Self-Guided Smartphone Walking Tour

Free cancellation available

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

Chicago Water Tower

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Fourth Presbyterian Church

Find out about the history of Chicago when you take a trip to Fourth Presbyterian Church. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

John Hancock Center

You can find out about the history of Chicago with a visit to John Hancock Center. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

St. James Cathedral

Find out about the history of Chicago with a stop at St. James Cathedral. Stroll along the riverfront or visit the notable monuments in this vibrant area.