Montgomery Vacation Packages

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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.

Top Montgomery Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
All staff were very friendly and helpful. Hotel was in convenient location for walking.

Reviewed on Jul. 27, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul. 21, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Great hotel! New build-out, spacious and clean, friendly staff. Excellent breakfast area with

Reviewed on Jul. 27, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
Very nicely decorated. The room was pretty small and didn’t have a small fridge. Was glad we brought a cooler.

Reviewed on Jul. 28, 2025

Ready to book your vacation to Montgomery?

 

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Montgomery Hotel Deals

DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Aug 3 to Aug 4
CA $114
CA $127 total
Aug 3 - Aug 4
includes taxes & fees
7.8/10 Good! (1,029 reviews)
"Was in central location and bed was nice and staff friendly"

Reviewed on Jul. 25, 2025

DoubleTree by Hilton Lisle Naperville
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
The price is CA $128 per night from Jul 29 to Jul 30
CA $128
CA $142 total
Jul 29 - Jul 30
includes taxes & fees
8.8/10 Excellent! (2,154 reviews)
"We have stayed at this hotel many times. Can't beat the price and location (close to everything). Breakfast very good."

Reviewed on Jul. 27, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
Motel 6 Naperville, IL

Motel 6 Naperville, IL

2 out of 5
1585 Naperville Wheaton Road, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is CA $78 per night from Aug 13 to Aug 14
CA $78
CA $87 total
Aug 13 - Aug 14
includes taxes & fees
7.8/10 Good! (1,015 reviews)
"Nice room"

Reviewed on Jul. 26, 2025

Motel 6 Naperville, IL
See all 575 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Frequently asked questions

How much does a Montgomery vacation package cost?
You'll find cheap prices from CA $1,195 on Expedia for your Montgomery getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Montgomery costs.
What are the cheapest months to go to Montgomery?
The off-season is the best time to travel to Montgomery if you're on a budget. Another tip for getting cheap Montgomery vacation packages? Avoid visiting during public holidays and any major festivals.
How many days is enough for Montgomery?
For a Montgomery vacation, a few days will be enough to tour the top spots. Make sure to stop by Hollywood Casino — it's one of the main sights in this destination. If you want more activities, think about basing yourself here and venturing off on some tours from Montgomery.
How to find the best Montgomery package deals?
Bagging a cheap Montgomery package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Montgomery package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Montgomery vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still get the freedom to create a customized Montgomery vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Montgomery?
If you're considering a spur-of-the-moment Montgomery adventure, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Montgomery?

  1. Choose your travel dates: What you want to do in Montgomery and your preferred season will help you decide when to get away.
  2. Set a budget: Factor in expenses like food, flights and transportation when calculating how much to put aside for your trip to Montgomery. Then, choose a hotel that matches your budget, whether that's a wallet-friendly stay or a more upscale retreat.
  3. Decide how long to go for: Now that you know more about Montgomery, you can figure out the perfect length of your vacation. Pull together a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Montgomery vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.