Montgomery Vacations from $580

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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $886, price is now $580 per person
$580
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.

Reviewed on May 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,597, price is now $1,002 per person
$1,002
per person
Jun 17 - Jun 21
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,127 reviews)
The breakfast menu was fresh, delicious, and there was such a good variety of items to choose from. The staff was pleasant & professional. Absolutely loved this hotel & will definitely vist again. There were tons of restaurants & shopping on the next block. Garretts popcorn right across the street from hotel. Hotel is beautiful & rooms were clean with lots of amenities. Great place to stay!

Reviewed on May 17, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,326, price is now $877 per person
$877
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.

Reviewed on May 14, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,107, price is now $746 per person
$746
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
Great view and room was very clean!

Reviewed on May 17, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,202, price is now $831 per person
$831
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

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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
$82 nightly
The price is $91 total per night from Jun 10 to Jun 11
$91 total
Jun 10 - Jun 11
Total with taxes and fees
9/10 Wonderful! (2,744 reviews)
Clean room fast service

Reviewed on May 16, 2026

SureStay Plus Hotel by Best Western Chicago Lombard
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 May 31 to Jun 1
$100 total
May 31 - Jun 1
Total with taxes and fees
7.2/10 Good! (1,568 reviews)
The room stunk so bad I couldn’t sleep!!! It was an old musty carpet smell. I even tried to spray Lysol but it only helped for about 5 minutes. I told the gentleman at the front desk and all he had to say was sorry I will tell my manager. Do not stay at this hotel it was truly gross!!!

Reviewed on May 17, 2026

Chicago Club Inn & Suites
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
$114 nightly
The price is $127 total per night from May 25 to May 26
$127 total
May 25 - May 26
Total with taxes and fees
8.2/10 Very Good! (1,567 reviews)
Our only let down was that not of the property doings. We just had very active next door neighbors that was a bit disturbing.

Reviewed on May 16, 2026

Embassy Suites by Hilton Chicago Lombard Oak Brook
See all 597 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 $580 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.