Montgomery Vacations from $371

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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.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was $608, price is now $371 per person
$371
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (468 reviews)
Room was amazing and beautiful and comfortable Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous

Reviewed on Mar 1, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,064, price is now $545 per person
$545
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Excellent value. Clean rooms, courteous staff, graat breakfast included.

Reviewed on Mar 12, 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 $662, price is now $393 per person
$393
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,575 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back.

Reviewed on Mar 4, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,206, price is now $730 per person
$730
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (436 reviews)
Great value, friendly staff

Reviewed on Mar 8, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $890, price is now $547 per person
$547
per person
May 19 - May 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
Loved how it was next to all the things you might need during a stay A grocery store convenience store and even a Walgreens down the street

Reviewed on Mar 12, 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
$74 nightly
The price is $82 total per night from Apr 3 to Apr 4
$82 total
Apr 3 - Apr 4
Total with taxes and fees
7.2/10 Good! (1,472 reviews)
The building caught fire while staying there. Every terrifying experience.

Reviewed on Mar 9, 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
$57 nightly
The price is $64 total per night from Mar 19 to Mar 20
$64 total
Mar 19 - Mar 20
Total with taxes and fees
6.4/10 (1,064 reviews)
Don't go there, it it really smell

Reviewed on Mar 11, 2026

Red Roof Inn PLUS+ Chicago - Willowbrook
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd Willowbrook IL
$137 nightly
The price is $144 total per night from Mar 16 to Mar 17
$144 total
Mar 16 - Mar 17
Total with taxes and fees
8.6/10 Excellent! (1,436 reviews)
Yes, the hot tub was fine and the parking was fine too. Everything was fine.

Reviewed on Mar 11, 2026

The Champagne Lodge & Luxury Suites
See all 593 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 $371 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.