Montgomery Holidays from £917

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Your Montgomery Holiday

When a getaway to the city is calling, answer it with a Montgomery holiday 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 holiday is just a few clicks away with Expedia.

Top Montgomery Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
23 Sept - 26 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,659 reviews)
Excellent establishment great staff very clean and spacious

Reviewed on 5 Aug 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Sept - 26 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
22 Oct - 29 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on 3 Aug 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
22 Oct - 29 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (270 reviews)
walkable to many desireable places.

Reviewed on 16 Jul 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
15 Oct - 22 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (332 reviews)
A lot of good food options walkable distance.

Reviewed on 3 Aug 2025

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

Top hotels in Montgomery

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 £74 per night from 31 Aug to 1 Sept
£74
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (2,159 reviews)
"K"

Reviewed on 5 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 £56 per night from 7 Sept to 8 Sept
£56
7 Sept - 8 Sept
includes taxes & fees
6.8/10 (1,244 reviews)
"Food is close to the room"

Reviewed on 6 Aug 2025

Chicago Club Inn & Suites
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 £69 per night from 17 Aug to 18 Aug
£69
17 Aug - 18 Aug
includes taxes & fees
7.8/10 Good! (1,059 reviews)
"We had a great time staying at DoubleTree in Naperville! The staff were friendly, welcoming, professional, and quick to address any issues that came up. They use text to check in on guests, and I shared a concern regarding an iron that wasn’t working - they quickly delivered a new one to my room. ..."

Reviewed on 4 Aug 2025

DoubleTree by Hilton Lisle Naperville
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 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.