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Top New Chicago Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,536, price is now CA $1,040 per person
CA $1,040
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
The front foyer had beautiful glass bulbs that were very dusty and dirty. Not a good first impression
Housekeeping or room service could have been disclosed for 4 nights garbage build up Also notice we had no bathroom hooks to hang wet towels just one towel bar.
Bed was comfortable and linens were fine.
Oh and, $8 bottle of Voss water in room no cups in room or bathroom. Microwave breakfast 😑
Reviewed on Jun 15, 2026

Pendry Chicago
Downtown Chicago
Price was CA $1,838, price is now CA $1,230 per person
CA $1,230
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
Beautiful hotel. Very clean which is very important to me. Couldn’t have asked for a more perfect location. Food and drink prices at the restaurant/bar were high. Other than that, would highly recommend.
Reviewed on Jun 16, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,943, price is now CA $1,367 per person
CA $1,367
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,535 reviews)
Great location and food court in area. Great for family fun
Reviewed on Jun 17, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,961, price is now CA $1,396 per person
CA $1,396
per person
Sep 2 - Sep 6
found 21 hours ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026

The Emily Hotel
Downtown Chicago
Price was CA $2,406, price is now CA $1,755 per person
CA $1,755
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
The staff was great. The room was nice but I would have preferred more towels. The remote in our room wasn’t working fully as well as the steamer in the room. Otherwise, it is a good hotel but would not recommend for families.
Reviewed on Jun 15, 2026
New Chicago Hotel Deals

Econo Lodge South Holland - Chicago Southland
17301 S Halsted St, Building B South Holland IL
Fully refundableReserve now, pay when you stay
The price is CA $89 per night from Jun 28 to Jun 29
CA $89
CA $101 total
Jun 28 - Jun 29
includes taxes & fees
6.2/10 (814 reviews)
"Great"
Reviewed on Jun 9, 2026

Days Inn and Suites by Wyndham Hammond, IN
4000 Calumet Avenue Hammond IN
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jun 29 to Jun 30
CA $127
CA $142 total
Jun 29 - Jun 30
includes taxes & fees
7.2/10 Good! (344 reviews)
"Whatever I needed they always were very helpful. Will definitely use this place again. My family had not one complaint."
Reviewed on Jun 16, 2026

Ameristar Casino Hotel East Chicago
777 Ameristar Blvd. East Chicago IN
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Jun 22 to Jun 23
CA $164
CA $200 total
Jun 22 - Jun 23
includes taxes & fees
8.6/10 Excellent! (1,031 reviews)
"The furniture needs to be updated rooms need to be cleaned better and rooms smell"
Reviewed on Jun 16, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







