
Montgomery Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 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
- Rest easyPlan, book, and manage your trip all in one place
Your Montgomery Vacation
When a getaway to the city is calling, answer it with a Montgomery vacation package. With all your travel arrangements worked out before you go, all you need to do here is focus on having a blast. A trip to Montgomery is a terrific opportunity to take in the sights. Be sure to visit renowned attractions like Aurora University, Hollywood Casino Aurora and Raging Waves Waterpark. Don't put off your visit to this city any longer. Your perfect Montgomery vacation is just a few clicks away with Expedia.
Top Montgomery Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Aloft Chicago Downtown River North
Downtown Chicago
Price was CA $816, price is now CA $643 per person
CA $643
per person
Apr 24 - Apr 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Staff was great but next to fire station. Beware very noisy if staying city view
Reviewed on Feb 8, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,468, price is now CA $985 per person
CA $985
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Housekeeper left hair shedding in room but overall amazing hotel and great staff
Reviewed on Feb 12, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,409, price is now CA $1,720 per person
CA $1,720
per person
Apr 2 - Apr 6
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

DoubleTree by Hilton Chicago - Alsip
Price was CA $1,188, price is now CA $880 per person
CA $880
per person
Apr 9 - Apr 15
found 16 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (MDW)
8.2/10 Very Good! (1,007 reviews)
Everything was perfect and the front desk was so nice
Reviewed on Feb 10, 2026

La Banque Hotel
Price was CA $1,157, price is now CA $884 per person
CA $884
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Montgomery Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Feb 17 to Feb 18
CA $98
CA $108 total
Feb 17 - Feb 18
includes taxes & fees
9/10 Wonderful! (2,555 reviews)
The entire staff was very accommodating and friendly. The rooms were very well stocked and clean. Less than 5 minutes(or less) away from dozens of restaurants and stores too.
Reviewed on Feb 12, 2026

The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
The price is CA $137 per night from Feb 17 to Feb 18
CA $137
CA $179 total
Feb 17 - Feb 18
includes taxes & fees
8.4/10 Very Good! (1,396 reviews)
The staff is so nice
Reviewed on Feb 10, 2026

Motel 6 Naperville, IL
1585 Naperville Wheaton Road Naperville IL
Fully refundableReserve now, pay when you stay
The price is CA $63 per night from Feb 17 to Feb 18
CA $63
CA $71 total
Feb 17 - Feb 18
includes taxes & fees
7.8/10 Good! (1,229 reviews)
It’s a very low-end hotel, to the point where they don’t have a fridge or microwave in the room. The walls are fairy thin and the bed wasn’t comfortable. But, it was very cheap and the front desk staff was very pleasant and courteous.
Reviewed on Feb 7, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.








