Montgomery Vacations from $156
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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.
The Latest Montgomery vacation packages
Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
Save 100% on your flight
Price was $261, price is now $156 per person
$156
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (384 reviews)
I like the place, it is very quiet and safe, but the room requires better cleaning, the balcony was not clean and blinds need to be washed, anyhow i liked it.
Reviewed on Aug 21, 2025
The Langham, Chicago
Downtown Chicago
Price was $3,789, price is now $2,161 per person
$2,161
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug 12, 2025
Homewood Suites by Hilton Chicago Downtown South Loop
Downtown Chicago
Save 100% on your flight
Price was $898, price is now $539 per person
$539
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,030 reviews)
Pros- Great area for walking, shopping, and eating. Corner rooms are big, my room was clean, and it had a view of Lake Michigan. Complimentary coffee, tea, and hot chocolate available in the hotel lobby.
Cons- You share the breakfast area, pool, gym, and laundry with the Hilton hotel connected to Home Suites and it gets REALLY crowded in those tight quarters during peak times.
The pros outweighed the cons though and I would stay here again.
Reviewed on Aug 23, 2025
The Stella Hotel & Ballroom
Downtown Kenosha
Save 100% on your flight
Price was $316, price is now $191 per person
$191
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (CHI)
9.4/10 Exceptional! (1,005 reviews)
Nice hotel, wish it had it's own parking lot.
Reviewed on Aug 23, 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $666, price is now $408 per person
$408
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,738 reviews)
It is a little bit too old , the location is perfect
Reviewed on Aug 25, 2025
Montgomery Hotel Deals
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Sep 7 to Sep 8
$92 total
Sep 7 - Sep 8
Total with taxes and fees
7.8/10 Good! (1,096 reviews)
"This was a horrible experience. The bedding was dirty and stained.. basically used. They provided a new room which smelled so bad we had to check out . The smell made my eyes & throat hurt and my daughter was getting a headache from the smell. We checked out and left the hotel. They said they would ..."
Reviewed on Aug 19, 2025
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $79 total per night from Sep 16 to Sep 17
$79 total
Sep 16 - Sep 17
Total with taxes and fees
8.8/10 Excellent! (2,200 reviews)
Quick trip
"The room was good for the time I spent in it. Breakfast was pretty good and convenient. Room was clean and the location was exactly what I needed."
Reviewed on Aug 25, 2025
Chicago Club Inn & Suites
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Sep 24 to Sep 25
$85 total
Sep 24 - Sep 25
Total with taxes and fees
7/10 Good! (1,239 reviews)
"Was good"
Reviewed on Aug 20, 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.
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.