
Gresham Holidays
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Price found within the past 48 hours. Click for updated prices.

Arlo Chicago
Downtown Chicago
Price was €944, price is now €565 per person
€565
per person
10 Nov - 16 Nov
found 11 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
I wish that all the staff was more accommodating! some of them were some were not!
Reviewed on 6 Oct 2025

Pendry Chicago
Downtown Chicago
Price was €1,201, price is now €678 per person
€678
per person
10 Nov - 16 Nov
found 11 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend
Reviewed on 7 Oct 2025

Swissotel - Chicago
Downtown Chicago
Price was €1,206, price is now €694 per person
€694
per person
10 Nov - 16 Nov
found 11 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
We stayed for a week and have 0 complaints. Great views, smelled good, nice staff and walkable to any bus or train
Reviewed on 8 Oct 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €1,040, price is now €643 per person
€643
per person
10 Nov - 16 Nov
found 11 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!
Reviewed on 7 Oct 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €1,089, price is now €682 per person
€682
per person
10 Nov - 16 Nov
found 11 hours ago
Return flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
Stayed for weekend anniversary, g
Reviewed on 8 Oct 2025
Where to stay in Gresham
Find the best Gresham areas and neighborhoods for the activities you enjoy most. Learn more about Gresham

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.
Top hotels in Gresham

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €128 per night from 2 Nov to 3 Nov
€128
2 Nov - 3 Nov
includes taxes & fees
7.8/10 Good! (9,286 reviews)
"The lobby is gorgeous! That being said our room….. the bathroom was falling apart. Our room felt like a cheap motel. The staff was extremely nice and helpful. The location is perfect."
Reviewed on 4 Oct 2025

Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €105 per night from 4 Nov to 5 Nov
€105
4 Nov - 5 Nov
includes taxes & fees
7.8/10 Good! (2,426 reviews)
"Excellent location, clean and good room partners"
Reviewed on 6 Oct 2025

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €168 per night from 4 Nov to 5 Nov
€168
4 Nov - 5 Nov
includes taxes & fees
8.4/10 Very Good! (5,052 reviews)
"good"
Reviewed on 7 Oct 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
€38
per adult
100% of travellers recommend

Chicago By Night River & Lake Cruise
€38
per adult
96% of travellers recommend

Chicago Sightseeing River and Lake Cruise
€38
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.