
Braidwood Holidays
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Top Flight + Hotel Deals in Braidwood
Price found within the past 48 hours. Click for updated prices.

Arlo Chicago
Downtown Chicago
Price was €617, price is now €476 per person
€476
per person
2 Jan - 6 Jan
found 15 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
The room was really clean and the staff was very friendly and accommodating
Reviewed on 10 Nov 2025

Pendry Chicago
Downtown Chicago
Price was €795, price is now €564 per person
€564
per person
2 Jan - 6 Jan
found 15 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Very nice, service was stellar, the bed was super comfortable, location perfect for our activities. Bar and resturaunt inviting and comfortable. We will definitely return on our next visit to Chicago.
Reviewed on 9 Nov 2025


theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €611, price is now €485 per person
€485
per person
2 Jan - 6 Jan
found 15 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early!
There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there.
This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.
Reviewed on 10 Nov 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was €648, price is now €519 per person
€519
per person
2 Jan - 6 Jan
found 15 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Great stay as always- beautiful property, rooms, Game Room is a gem, and excellent staff; just a couple notes:
Bring back The Milk Room!
The lobby seating was less inviting with so much turned over to assigned-seating dining.
Can the hotel offer at least complimentary coffee/tea for guests? I prepaid for breakfast but still had to pay $5 per cup of coffee.
Reviewed on 9 Nov 2025
Top hotels in Braidwood

Red Roof Inn Chicago - Joliet
1750 Mcdonough St, Joliet, IL
Fully refundableReserve now, pay when you stay
The price is €54 per night from 12 Nov to 13 Nov
€54
12 Nov - 13 Nov
includes taxes & fees
6.6/10 (1,000 reviews)
Yes
Reviewed on 3 Nov 2025

Wingate by Wyndham - Joliet
101 McDonald Avenue, Joliet, IL
Fully refundableReserve now, pay when you stay
The price is €72 per night from 7 Dec to 8 Dec
€72
7 Dec - 8 Dec
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
Parking was easy. The room was clean. I wish the beds were a little more comfortable. Other than that, I would stay here again
Reviewed on 8 Nov 2025

Super 8 by Wyndham Joliet
1806 McDonough St, Joliet, IL
Fully refundableReserve now, pay when you stay
The price is €81 per night from 16 Nov to 17 Nov
€81
16 Nov - 17 Nov
includes taxes & fees
8/10 Very Good! (713 reviews)
Motel has roaches
Reviewed on 8 Nov 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.
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