Montgomery Holidays from £995

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Your Montgomery Holiday

History, cuisine, art and more … It's all waiting for you with a Montgomery holiday package. And with the ability to customize your city adventure, it's guaranteed to be one you won't forget. Aurora University, Hollywood Casino Aurora and Paramount Theatre are just some of the many attractions worth visiting during your trip to Montgomery. Whoever you're taking time off with and whatever your budget, your ultimate Montgomery holiday is just a few clicks away with Expedia.

The Latest Montgomery Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on 10 Jan 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Good location, nice vibe, amazing staff!

Reviewed on 30 Apr 2024

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
5 Jun - 13 Jun
Return flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,784 reviews)
The AC quit working in the middle of the night and no soap in the shower. Otherwise everything was top notch and we loved our stay.

Reviewed on 30 Apr 2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (1,056 reviews)
Very nice Hotel in the best location

Reviewed on 2 May 2024

Kimpton Hotel Monaco Chicago, an IHG Hotel

Kimpton Hotel Monaco Chicago, an IHG Hotel

4.5 out of 5
Downtown Chicago
per person
19 Jun - 23 Jun
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Nice neighborhood with great restaurant close by. Style of hotel was cool with window seat, great views.

Reviewed on 29 Apr 2024

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
per person
5 Jun - 13 Jun
Return flight included
London (LON) to Chicago (ORD)
7.8/10 Good! (1,765 reviews)
The hotel was nice and clean and located in a good area

Reviewed on 2 May 2024

Montgomery Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
19,500
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Raging Waves Waterpark, Paramount Theatre and Splash Country Waterpark

Our pick of the best Montgomery Hotel Deals

Chicago Club Inn & Suites
Chicago Club Inn & Suites
3 out of 5
630 Pasquinelli Dr, Westmont, IL
Stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi and free parking. Our guests praise the clean rooms in their reviews. Popular ...
6/10 (1,004 reviews)
"I enjoyed my stay hotel was quiet and clean"

Reviewed on 29 Apr 2024

Chicago Club Inn & Suites
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
Stay at this business-friendly hotel in Lombard. Enjoy free breakfast, free parking and WiFi. Our guests praise the breakfast and the helpful staff in their ...
8.6/10 Excellent! (1,496 reviews)
"It was okay. Breakfast could be better"

Reviewed on 29 Apr 2024

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
Stay at this 4-star business-friendly hotel in Naperville. Enjoy free WiFi, free parking and breakfast. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (991 reviews)
"Awesome jacuzzi and customer service"

Reviewed on 1 May 2024

DoubleTree by Hilton Lisle Naperville
See all 616 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Montgomery holiday with Expedia?
Expedia has you covered for every aspect of your next Montgomery getaway. You’ll always get the best prices around, but when you bundle your accommodation, flights and/or hire car into a holiday package, you can save even more. Want to really make the most of your escape? Add a few exciting activities and tours to your package. Expedia offers flexible cancellation policies on most bookings, so you won’t need to worry if you have to change your plans. Head over to our Customer Service Portal link to find out more.
When is the best time of year to holiday in Montgomery?
If you enjoy the excitement that comes with peak season, head to Montgomery in May, July and August. If you’d like a more relaxed vibe, December, January and February will suit you better. Plan your visit to Montgomery based on what type of holiday you want. January is the coolest month, when average daytime temperatures are -4ºC. In July, the warmest period, expect averages of 23ºC during the day.
What are the top hotels for my holiday in Montgomery?
Many travellers like to stay at Entire 3bd/1.5bath home/Private/FREE Wifi in Boulder Hill. If it’s your first visit to Montgomery, you’ll receive a warm welcome here.
How do I get a cheap holiday to Montgomery?
Bundle your flights and hotels, toss in extras such as a hire car or activities, and save with a Montgomery holiday. You won’t just enjoy superb discounts on your adventure — you’ll have loads of choice at your fingertips too. When you book through Expedia, you’ll have your pick of over 400 airlines and 321,000 hotels throughout the world. Your next epic adventure begins right here, right now! Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Montgomery holiday?
Make sure your holiday in Montgomery is a memorable one by taking in its well-known attractions. Chicago Premium Outlets, Aurora University, Raging Waves Waterpark and Paramount Theatre are among the things to put on your itinerary while you’re in the area.
Do I need a visa for my Montgomery holiday?
Visa requirements for Montgomery vary depending on your nationality and the reason for your visit. Remember to check official government websites to determine if you need a visa for your trip. This is also a good place to find the most up-to-date information, including details about application procedures and any supporting documentation that may be necessary. Research your visa requirements well ahead of time to ensure a smooth travel experience. Also double-check to see that your passport is valid for a further six months from your planned date of return.
What should I wear on my Montgomery holiday?
Though everyone’s style is different, it can be helpful to have some guidelines for what kind of clothes to wear during your holiday in Montgomery. We recommend looking up social media before you head off to get inspiration for local fashion trends. Have a look at the local weather forecast so you can pack appropriately. The warmest month in Montgomery is July, with average daytime temperatures of 23ºC. If you’re visiting in the coolest month of January, the mercury hovers around -4ºC during the day.
What does an Expedia Montgomery holiday include?
Hotels, flights and a reliable car for all your fun road trip adventures. Simply mix and match your preferred bundle and get access to great discounts. Once you’ve made your booking, add on some activities and tours and watch your savings pile up. When it comes to crafting your Montgomery holiday, you’re the boss! Private holiday homes and apartments are a few of the most sought-after property types in Montgomery. Whatever your holiday style or group size, you can rely on Expedia for the freedom to personalise your next big adventure.
Does Expedia offer Book Now, Pay Later Montgomery holidays?
We certainly do. Expedia has teamed up with online lender Klarna to help you easily pay for your trip in manageable instalments. Simply select the payment plan that suits best during checkout and take away the stress of budgeting for your next trip. Be sure to bundle your flights, accommodation and activities with Expedia to get the biggest bang for your holiday buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all types of budgets, so you can lock in that well-deserved holiday sooner.
  • No-deposit holidays: Clicking the “book now” button is much easier with this payment plan. With no deposit required for your getaway, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Montgomery Expedia holiday?
You can, and with over 400 airlines to choose from worldwide, you’re not short on choice. Look through the available options and see which airline fits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.