Montgomery Vacations from ₩491,260

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The Latest Montgomery Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
per person
Aug 13 - Aug 15
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.4/10 Very Good! (4,263 reviews)
I like the breakfast

Reviewed on Jul 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 13 - Aug 15
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Beautiful!! Location, room, security, everything was perfect! Very classy, elegant!

Reviewed on Jul 9, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 13 - Aug 15
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
It’s a great location for walk around the beautiful downtown of Chicago. People were so helpful and friendly. Definitely I’ll consider coming back.

Reviewed on Jul 7, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 13 - Aug 15
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,097 reviews)
Spacious room with a very comfortable bed, comfortable room temperature on a hot weekend, large bathroom and spacious work station. Close to trains that transport to the loop within minutes.

Reviewed on Jul 8, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Aug 13 - Aug 15
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
Great staff, very good breakfast and well located hotel. Room was clean and comfortable. My only suggestion would be to double check the utensils are clean before put them on the buffet area because I founded some residual food in a couple dishes. Other than that we have a great stay and definitely would stay here again.

Reviewed on Jul 8, 2025

Find the Best Montgomery Vacation Packages

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
The price is ₩116,596 per night from Jul 10 to Jul 11
₩116,596
₩129,398 total
Jul 10 - Jul 11
includes taxes & fees
8.8/10 Excellent! (2,100 reviews)
"Staff are always nice and helpful. Rooms and property are clean and comfortable"

Reviewed on Jul 7, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
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 ₩114,140 per night from Jul 20 to Jul 21
₩114,140
₩126,673 total
Jul 20 - Jul 21
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"It was nice and clean and the beds were comfy"

Reviewed on Jul 5, 2025

DoubleTree by Hilton Lisle Naperville
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 ₩65,151 per night from Jul 24 to Jul 25
₩65,151
₩72,628 total
Jul 24 - Jul 25
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"The place is good value for the money"

Reviewed on Jun 22, 2025

Motel 6 Naperville, IL
See all 576 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.

Frequently asked questions

How much does a Montgomery vacation package cost?
You can snap up a vacation package to this destination from ₩491,260 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?
The off-season is the best time to head to Montgomery if you're trying to keep costs down. Another tip for getting cheap Montgomery vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Montgomery?
The ideal length of your Montgomery vacation depends on what you'd like to do. Generally, a few days to a week will give you time to check out all the major sights and discover some hidden spots along the way.
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.
How to plan a trip to Montgomery?

  1. Choose when to get away: Check your diary and pack your bags. Your favorite time of year and the available activities will also help you decide when to visit Montgomery.
  2. Set a budget: Consider expenses like flights, transportation and food when working out how much to put aside for your trip to Montgomery. Then, select a hotel that works with your budget, whether that's an affordable stay or a more upscale getaway.
  3. Decide how long to go away for: Now that you're more familiar with Montgomery, you can figure out the ideal length of your break. Put together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Montgomery vacation package.

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