Montgomery Vacations from $239

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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.
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 $403, price is now $239 per person
$239
per person
May 10 - May 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The bar was fine we got 2 free drinks.

Reviewed on Apr 1, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,398, price is now $731 per person
$731
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer. Buffet breakfast is included and that makes it very good value. Hotel also has a gym/ Not too many amenities in the room though.

Reviewed on Apr 2, 2026

Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
Downtown Evanston
Price was $629, price is now $437 per person
$437
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,818 reviews)
I love this hotel. Check-in was pleasant, efficient, and the hotel's amenities were nicely highlighted. I was blessed to be granted a room on the south side ofbthe building

Reviewed on Mar 31, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $994, price is now $693 per person
$693
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,862 reviews)
Nice staff, clean rooms, however elevator is slow

Reviewed on Apr 2, 2026

Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Price was $623, price is now $445 per person
$445
per person
Jun 24 - Jun 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8/10 Very Good! (504 reviews)
Waited 15min to check in. Received an apology along with an explanation of having to do three jobs at once. Shower ceiling had peeling paint with mildew/mold stains. Vanity would not drain. Was relocated to another RM.

Reviewed on Apr 1, 2026

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Montgomery Hotel Deals

Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $100 total per night from Apr 5 to Apr 6
$100 total
Apr 5 - Apr 6
Total with taxes and fees
7.2/10 Good! (1,496 reviews)
Love breakfast

Reviewed on Apr 2, 2026

Chicago Club Inn & Suites
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
$56 nightly
The price is $62 total per night from Apr 18 to Apr 19
$62 total
Apr 18 - Apr 19
Total with taxes and fees
6.4/10 (1,083 reviews)
Not at all what the pictures show. The whole place is decrepit and falling apart. Another guest was walking their dog and did not clean up after it.

Reviewed on Mar 30, 2026

Red Roof Inn PLUS+ Chicago - Willowbrook
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
707 E Butterfield Road Lombard IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $118 total per night from Apr 5 to Apr 6
$118 total
Apr 5 - Apr 6
Total with taxes and fees
8.2/10 Very Good! (1,459 reviews)
Check-in was easy, and quick. Room was clean. Whirlpool was closed.. it was fine until everyone got in their rooms. Kids were loud lots of thumping. Ceiling leaking in the main lobby. But other than that. All was good. Thanks for the stay!

Reviewed on Apr 2, 2026

Embassy Suites by Hilton Chicago Lombard Oak Brook
See all 596 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 $239 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.