Montgomery Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Montgomery

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 S$118 per night from 24 Aug to 25 Aug
S$118
24 Aug - 25 Aug
includes taxes & fees
7.8/10 Good! (1,079 reviews)
"Cool place"

Reviewed on 13 Aug, 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 S$101 per night from 16 Sept to 17 Sept
S$101
16 Sept - 17 Sept
includes taxes & fees
8.8/10 Excellent! (2,175 reviews)
"Nice"

Reviewed on 15 Aug, 2025

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
The price is S$103 per night from 15 Sept to 16 Sept
S$103
15 Sept - 16 Sept
includes taxes & fees
7/10 Good! (1,234 reviews)
"I liked the accessibility to the pool."

Reviewed on 9 Aug, 2025

Chicago Club Inn & Suites
See all 572 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 holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday 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 holiday 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 holiday 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," "Traveller 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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can personalise 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 holiday package to Montgomery?
If you've got your Montgomery holiday 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 favourite 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 customised Montgomery holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.