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theWit Chicago, a Hilton Hotel

Downtown Chicago

HK$5,936

per person

2 Nov - 6 Nov

found 1 day ago

Return flight included

San Juan (SJU) to Chicago (ORD)

9/10 Wonderful! (1,004 reviews)

The room was perfect and the front staff were exceptional. Our stay was amazing!

Reviewed on 21 Sept 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

HK$9,029

per person

2 Nov - 6 Nov

found 1 day ago

Return flight included

San Juan (SJU) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.

Reviewed on 24 Sept 2025

The Emily Hotel

Downtown Chicago

HK$6,983

per person

2 Nov - 6 Nov

found 1 day ago

Return flight included

San Juan (SJU) to Chicago (ORD)

9.2/10 Wonderful! (1,222 reviews)

I was so disappointed in my stay at the Emily. For almost $500/night I was expecting nice, spacious rooms. The room was so small, the sink was in the hallway, the bed was so uncomfortable, dingy design. I’ve stayed at better Aloft or Moxy rooms. The food at Fora, the hotel restaurant, is uninspired and unseasoned. The brunch chiliques were bland. Skip this hotel in west loop and stay at the hoxton instead

Reviewed on 22 Sept 2025

Tours & day trips

See all 164 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 29 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 29 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 17 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Chicago Bulls Basketball Game at United Centre

Popular places to visit

Rookery

Built by famed 19th-century architects and renovated in 1907 by Frank Lloyd Wright, this early skyscraper is a great stop on a Chicago architecture tour.

Chicago Board of Trade Building

You can learn about the history of Chicago when you stop by Chicago Board of Trade Building. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.

Printer\'s Row showing a city and heritage architecture

Harold Washington Library Center

Harold Washington Library Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Discover the fascinating museums and notable monuments in this vibrant area.

CIBC Theatre

You can enjoy a show at CIBC Theatre on your trip to Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Chase Tower

You can find out about the history of Chicago with a visit to Chase Tower. Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Chicago Loop Synagogue

Chicago Loop Synagogue is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.