Montgomery Holidays from £1,308

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,959, price is now £1,308 per person
£1,308
per person
4 Sept - 11 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Location

Reviewed on 10 Jul 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,703, price is now £1,644 per person
£1,644
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
I thoroughly enjoyed my stay at Hotel Felix! While it may not technically be a five-star luxury chain, it definitely gave us five-star hotel vibes thanks to the incredible staff and the fantastic extra perks.The location is absolutely awesome. It puts you about a mile or so from all the major hotspots, including Navy Pier, the Riverwalk, and the Magnificent Mile. There are tons of excellent places to eat right nearby, and having a Divvy bike rental station right down the street made exploring the city incredibly easy.The service from the staff was top-notch from start to finish. I highly recommend this hotel for anyone looking for a stylish, perfectly located, and highly accommodating place to stay in Chicago!

Reviewed on 13 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,642, price is now £1,672 per person
£1,672
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Clean rooms, nice pool, location great

Reviewed on 12 Jul 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was £2,363, price is now £1,503 per person
£1,503
per person
13 Sept - 20 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (635 reviews)
Great location and amazing AC in the room

Reviewed on 12 Jul 2026

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
Price was £2,733, price is now £1,806 per person
£1,806
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Booked this stay for my husband Birthday. Wanted to make sure he enjoyed himself as well as me. I spent over $800 for the corner room, check in is at 4pm and we arrived about 430ish. Got to the room and the Amenities I purchased wasn’t there which was $100(they stated it would be at 4pm) which is why I want to arrive later. I noticed that the bed sheets were ripped, small stains on the couch in front of bed and the seat in the corner by the window that creeped me out. So we left and via Hilton app I contacted the Hotel to find out why my paid Amenities wasn’t there and they sat them in there while we were gone to dinner. We got back and the chocolate covered strawberries were melted. The best part about the stay was the firework show. My husband and I enjoyed ourselves as best we could after noticing these issues it was disgusting seeing the stains and the ripped sheets especially paying what was over $1000 for one night

Reviewed on 13 Jul 2026

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

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 11 Aug to 12 Aug
£56
11 Aug - 12 Aug
includes taxes & fees
7.2/10 Good! (1,647 reviews)
"The balcony was nice to get fresh air on"

Reviewed on 12 Jul 2026

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
Fully refundableReserve now, pay when you stay
The price is £73 per night from 3 Aug to 4 Aug
£73
3 Aug - 4 Aug
includes taxes & fees
9/10 Wonderful! (2,883 reviews)
"Everything was good, as this is our 3rd or 4th time at this hotel. But this was the first time we had a first floor accommodation. And the only problem we encountered were ants crawling on the table to get to our fountain pops."

Reviewed on 11 Jul 2026

SureStay Plus Hotel by Best Western Chicago Lombard
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
The price is £58 per night from 19 Jul to 20 Jul
£58
19 Jul - 20 Jul
includes taxes & fees
6.4/10 (1,192 reviews)
"The room looks like it wasn’t even cleaned, the sheets weren’t white anymore, towels were very thin. Parking is Ok, staff is pretty responsive."

Reviewed on 11 Jul 2026

Red Roof Inn PLUS+ Chicago - Willowbrook
See all 551 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.

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* 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.