
Greater Grand Crossing Vacations from ¥255,376
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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The Latest Greater Grand Crossing Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Pendry Chicago
Downtown Chicago
Price was ¥295,904, price is now ¥255,376 per person
¥255,376
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.
Reviewed on Nov 18, 2025

The Westin Michigan Avenue Chicago
Downtown Chicago
Price was ¥371,466, price is now ¥260,622 per person
¥260,622
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
17.6/10 Exceptional! (1,074 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.
Reviewed on Nov 17, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥402,036, price is now ¥316,946 per person
¥316,946
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance.
The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return.
Mr. & Mrs.S
Reviewed on Nov 17, 2025

Park Hyatt Chicago
Downtown Chicago
Price was ¥383,892, price is now ¥316,307 per person
¥316,307
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
19.2/10 Exceptional! (1,000 reviews)
Stay was amazing!!! The staff was so friendly, kind, and thoughtful! The rooms were soooo beyond perfect and lovely! And the food at the restaurant was amazing.. especially breakfast! You won’t regret staying here!!!
Reviewed on Nov 18, 2025

Level Chicago – Old Town
Downtown Chicago
Price was ¥330,520, price is now ¥277,395 per person
¥277,395
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
18/10 Exceptional! (380 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
Where to stay in Greater Grand Crossing
Find the best Greater Grand Crossing areas and neighborhoods for the activities you enjoy most. Learn more about Greater Grand Crossing

Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Greater Grand Crossing Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is ¥13,477 per night from Dec 9 to Dec 10
¥13,477
¥15,819 total
Dec 9 - Dec 10
includes taxes & fees
8.4/10 Very Good! (5,268 reviews)
Rooms are clean. Personal great. Breakfast excellent. 💯 recommended 👌
Reviewed on Nov 17, 2025

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥16,348 per night from Nov 24 to Nov 25
¥16,348
¥23,056 total
Nov 24 - Nov 25
includes taxes & fees
8.4/10 Very Good! (2,065 reviews)
Classy and classic! Never disappoints
Reviewed on Nov 16, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥12,934 per night from Dec 7 to Dec 8
¥12,934
¥15,184 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,324 reviews)
Awesome location and valet was very helpful
Reviewed on Nov 18, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Things to do

Skydeck - Willis Tower Admission
¥6,717
per adult
96% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
¥3,749
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




