New Chicago Vacation Packages
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Top New Chicago Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was CA $1,839, price is now CA $1,245 per person
CA $1,245
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
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
just found
Roundtrip flight included
Toronto (YTO) 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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,959, price is now CA $1,384 per person
CA $1,384
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 Fulton Market
Downtown Chicago
Price was CA $2,654, price is now CA $1,953 per person
CA $1,953
per person
Aug 24 - Aug 28
found 22 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.
Reviewed on Jun 14, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,235, price is now CA $1,664 per person
CA $1,664
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Fantastic, attentive staff. Beautiful facilities.
Reviewed on Jun 17, 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 Jul 6 to Jul 7
CA $89
CA $101 total
Jul 6 - Jul 7
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.
