
Greater Grand Crossing Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Where to stay in Greater Grand Crossing

Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Top hotels in Greater Grand Crossing

Congress Plaza Hotel
"Great location. Walkable to all the downtown attractions. Historical hotel with updated rooms. Highly recommend."
Reviewed on 23 May, 2026

Hotel Riu Plaza Chicago
"The room is clean. The location is great with many nice shops nearby, including the Starbucks Reserve Roastery. It’s within walking distance to Navy Pier, Willis Tower, boat ride and many other architectural marvels. The breakfast is good with some variations each day. The staff are generally friendly ..."
Reviewed on 24 May, 2026

The Chicago Hotel Collection - Magnificent Mile
"Excellent location within walking distance of bars , restaurants and transit. Clean and spacious rooms."
Reviewed on 24 May, 2026
Frequently asked questions
Things to do

Skydeck - Willis Tower Admission
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.





