Montgomery Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Swissotel - Chicago
Downtown Chicago
CA $1,062
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
It was very nice and was by a lot of attractions and i definitely recommend taking a boat ride near by !
Reviewed on Aug 21, 2026
The Talbott, Autograph Collection
Downtown Chicago
CA $1,447
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in.
4 days later, the on-line booking co. Said the manager did not agree to release my reservation.
Unethical procedurers.
Reviewed on Aug 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,339
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Incredible hotel — it was clean, the room was spacious, the staff were incredibly friendly, and it was conveniently located in the heart of downtown, within walking distance of everything we needed.
Reviewed on Aug 21, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $1,988
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on Aug 16, 2026
Ready to book your vacation to Montgomery?
Montgomery Hotel Deals
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
CA $87
CA $97 total
Sep 3 - Sep 4
includes taxes & fees
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
CA $77
CA $86 total
Sep 22 - Sep 23
includes taxes & fees
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
CA $118
CA $131 total
Sep 3 - Sep 4
includes taxes & fees
7.8/10 Good! (1,434 reviews)
"The property is under renovation and has a few shortcomings. The staff is Amazing. They assisted in all our needs. Ms. Natalie at the front desk is professional and cheerful. Thanks. She was easy to talk to and was genuinely helpful."
Reviewed on Aug 21, 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.
Frequently asked questions
How much does a Montgomery vacation package cost?
You'll find cheap prices from CA $1,062 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?
- Choose your travel dates: What you want to do in Montgomery and your preferred season will help you decide when to get away.
- 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.
- 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.
- 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.
