Montgomery Vacation Packages
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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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,870, price is now CA $1,271 per person
CA $1,271
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
The breakfast menu & service at the Lyrica was excellent. The parking was very convenient, although a little pricey at $65 for overnight. The rooms and view were simply awesome. The service at the front desk was excellent. I look forward to my next stay.
Reviewed on May 20, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,763, price is now CA $1,251 per person
CA $1,251
per person
Jul 23 - Jul 26
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,126 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,513, price is now CA $1,789 per person
CA $1,789
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,864 reviews)
Great experience! Would stay here agin
Reviewed on May 18, 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 $127 per night from Jun 3 to Jun 4
CA $127
CA $141 total
Jun 3 - Jun 4
includes taxes & fees
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from May 25 to May 26
CA $111
CA $124 total
May 25 - May 26
includes taxes & fees
7.2/10 Good! (1,573 reviews)
"Stayed Friday-Monday in a room with a hot tub. The jets in the hot tub are extremely forceful. Water pressure strong in bathroom as well. Fridge and microwave good. Only one electric outlet near the bed. Kept hitting the metal frame of the bed when i got in and out of it which was annoying. Ice machine ..."
Reviewed on May 20, 2026
Embassy Suites by Hilton Chicago Lombard Oak Brook
707 E Butterfield Road Lombard IL
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from May 31 to Jun 1
CA $176
CA $195 total
May 31 - Jun 1
includes taxes & fees
8.2/10 Very Good! (1,574 reviews)
"Omelettes were delicious"
Reviewed on May 18, 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.
