Montgomery Vacations from $374

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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.

The Latest Montgomery vacation packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $594, price is now $374 per person
$374
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,076, price is now $558 per person
$558
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all

Reviewed on Feb 2, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $712, price is now $415 per person
$415
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.

Reviewed on Feb 2, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $642, price is now $397 per person
$397
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $646, price is now $412 per person
$412
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (3,098 reviews)
Nice location, friendly staff and room was nice

Reviewed on Feb 3, 2026

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Montgomery Hotel Deals

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Feb 5 to Feb 6
$85 total
Feb 5 - Feb 6
Total with taxes and fees
9/10 Wonderful! (2,547 reviews)
Very satisfied

Reviewed on Feb 3, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
$124 nightly
The price is $130 total per night from Feb 9 to Feb 10
$130 total
Feb 9 - Feb 10
Total with taxes and fees
8.4/10 Very Good! (1,390 reviews)
Everything was outstanding

Reviewed on Feb 3, 2026

The Champagne Lodge & Luxury Suites
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $80 total per night from Feb 9 to Feb 10
$80 total
Feb 9 - Feb 10
Total with taxes and fees
7/10 Good! (1,417 reviews)
Fantastic place to stay. Friendly staff. Daily free breakfast with many choices. Rooms very clean. Will definitely return there for a stay.

Reviewed on Feb 2, 2026

Chicago Club Inn & Suites
See all 603 properties in Montgomery
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.

Find the Best Montgomery Vacation Packages

Montgomery Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
19,500
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Paramount Theater, Sugar Grove Family Fun Center and Splash Country Waterpark

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Frequently asked questions

How much does a Montgomery vacation package cost?
You can snap up a vacation package to this destination from $374 on Expedia. However, how much your vacation to Montgomery costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Montgomery?
December, January and February are great times to look for cheap Montgomery vacation packages. Choosing to travel in less busy months means you can typically find reduced prices on hotels and flights.
How many days is enough for Montgomery?
Usually, a handful of days is enough to see the major sights during your Montgomery vacation. But if you prefer to have time to rest or take day tours, consider extending your trip.
How to find the best Montgomery package deals?
Bagging a cheap Montgomery package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Montgomery package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Montgomery vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and accommodations individually. Better still, you can personalize your Montgomery escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Montgomery?
If you've got your Montgomery vacation dates finalized, book early to snap up some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Montgomery vacation packages?
If you're like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Montgomery trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.