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theWit Chicago, a Hilton Hotel

Downtown Chicago

HK$5,936

per person

2 Nov - 6 Nov

found 22 hours 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 22 hours 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 22 hours 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 163 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 16 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

Clarke House Museum

You can spend time studying the exhibits at Clarke House Museum during your travels in Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

Glessner House Museum

You can spend time exploring the galleries in Glessner House Museum during your trip to Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

Chess Records Building / Blues Heaven

You can spend time exploring the galleries in Chess Records Building / Blues Heaven during your trip to Chicago. While in this vibrant area, you can savour the top-notch restaurants.

Willie Dixon's Blues Heaven

You can learn about the history of Chicago with a visit to Willie Dixon's Blues Heaven. Stroll along the lakeside or visit the notable monuments in this vibrant area.

South Asia Institute

You can spend time exploring the galleries in South Asia Institute during your trip to Chicago. While in this vibrant area, you can savour the top-notch restaurants.