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theWit Chicago, a Hilton Hotel

Downtown Chicago

HK$5,936

per person

2 Nov - 6 Nov

found 24 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 24 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 24 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 164 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 30 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

St. James Cathedral

St. James Cathedral 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 visit the notable monuments in this vibrant area.

Holy Name Cathedral

After visiting Holy Name Cathedral, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Shops at North Bridge

Spend a day exploring the department store, luxury fashion outlets and food court at this mall on the glitzy Magnificent Mile shopping district.

Shops at Northbridge

You can find the perfect gifts to bring home at Shops at Northbridge during your trip to Chicago. Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Magnificent Mile - River North featuring night scenes, a city and signage

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Tribune Tower

You can learn about the history of Chicago with a visit to Tribune Tower. Discover the fascinating museums and notable monuments in this vibrant area.