Montgomery Vacations from $534
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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 Fulton Market
Downtown Chicago
$793
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Great staff and amenities. Beautiful pool, bbq area and more. Terrific room
Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day
As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them.
For the money your room key or a key pad should allow you in.
Reviewed on Aug 21, 2026
Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
$616
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,123 reviews)
The room was very nice. More spacious than expected. And was very Clean and comfortable. Pillows and bedding all
Very nice. Key cards worked well. Enough space to not feel cramped. AC ran well and kept room comfortable throughout day and night. Check in was easy. Representatives were friendly. And helpful in holding our luggage so we can walk around this beautiful city. Definitely recommend this hotel. Free Coffee and free water in the lobby was a nice touch.
Reviewed on Aug 23, 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
$875
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,348 reviews)
Great hotel front desk very nice and informative close walking distance to public transportation and stores. If you don’t valet parking garages 1-2 blocks away for self parking.
Reviewed on Aug 22, 2026
Montgomery Hotel Deals
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
$62 nightly
$69 total
Aug 31 - Sep 1
Total with taxes and fees
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
$64 nightly
$71 total
Sep 21 - Sep 22
Total with taxes and fees
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
$86 nightly
$96 total
Aug 30 - Aug 31
Total with taxes and fees
7.8/10 Good! (1,436 reviews)
"The hotel is under construction. I thought that meant maybe they’d have guests on one floor and construction on another. No. Housekeeping tried to enter our room at 8 AM while we were asleep. Construction began at 8:05, directly through our wall. We should not have been placed there. Amenities like ..."
Reviewed on Aug 23, 2026
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 $534 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.
