Montgomery Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Montgomery Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
8.4/10 Very Good! (1,387 reviews)
Beautiful hotel, quiet clean spacious rooms! Breakfast buffett to die for. Close to museums and Metro.

Reviewed on 24 Nov,2024

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (931 reviews)
We had multiple issues with the locks on our door.

Reviewed on 24 Nov,2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!

Reviewed on 11 Nov,2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (809 reviews)
Lobby and shared space downstairs is beautiful and location is great in Fulton Market. We walked to many bars and restaurants and enjoyed the vibe. The rooms are underwhelming, no closet space, bathroom space lacking, and feel dated despite trying to go for a modern-industrial-chic vibe. The quality of the rooms do not match what the lobby area indicates. The hallways seem like they didn’t get touched in whatever remodel happened here. Overall I think it’s overpriced for what it delivers.

Reviewed on 20 Nov,2024

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (1,378 reviews)
Andy at the front desk was amazing and so professional! Just based on the service he provided, I will be back! Hotel is in an excellent location as well! Would definitely recommend!

Reviewed on 25 Nov,2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Montgomery

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 S$88 per night from 2 Dec to 3 Dec
S$88
includes taxes & fees
2 Dec - 3 Dec
6.2/10 (1,000 reviews)
"VERY NICE ND CLEAN ND QUIET"

Reviewed on 18 Nov,2024

Red Roof Inn PLUS+ Chicago - Willowbrook
The Champagne Lodge & Luxury Suites
The Champagne Lodge & Luxury Suites
3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is S$175 per night from 2 Dec to 3 Dec
S$175
includes taxes & fees
2 Dec - 3 Dec
8.4/10 Very Good! (1,011 reviews)
"The hot tub, fire place ambiance steam room. Love it"

Reviewed on 24 Nov,2024

The Champagne Lodge & Luxury 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 S$118 per night from 1 Dec to 2 Dec
S$118
includes taxes & fees
1 Dec - 2 Dec
7.8/10 Good! (1,007 reviews)
"Has its own restaurant and bar"

Reviewed on 24 Nov,2024

DoubleTree by Hilton Lisle Naperville
See all 527 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?
Get ready to book, because a getaway to Montgomery starts from an enticing S$757. When you bundle your hotels, flights and car rentals into a travel package, you’ll score great deals.
How do I get a cheap travel package to Montgomery?
Bundle your hotel and flight bookings, add extras such as a rental car or activities, and save with a Montgomery holiday package. You won’t just score big discounts on your getaway — you’ll have lots of choice at your fingertips too. When you book through Expedia, you can choose from more than 550 partner airlines and 1,000,000 properties worldwide. Your next grand adventure begins right here, right now!
Where should I stay in Montgomery?
A holiday in Montgomery isn’t complete without checking out Aurora University, Hollywood Casino Aurora and Paramount Theatre. Stay close to these sights and make sightseeing a breeze.
What are the top hotels in Montgomery?
Glamorous Apartment In Montgomery will make an excellent base for your Montgomery escape. Situated in Boulder Hill, it’s one of this area’s best hotels.
How far in advance should I book my Montgomery holiday?
While prices fluctuate, we generally recommend booking your spot as early as possible. Many international fares can be found on Expedia up to a year in advance. If you’re booking late, you might still be lucky. Low prices to Montgomery sometimes emerge just weeks before departure.
What does an Expedia Montgomery travel package include?
Expedia has everything you need to lock in Montgomery getaway, but what your package looks like is entirely up to you. Select from a combination of rental cars, flights and hotels. After some tours or experiences to keep you entertained? Once you’ve made your booking, you can add them on too. Whatever your style, there’s a holiday package to suit your needs.
Can I choose my airline with a Montgomery Expedia holiday package?
Yes, of course. Expedia has access to more than 550 partner airlines worldwide, so pick the carrier that’s a good fit for your travel preferences.
If I'm not able to travel, can I cancel my Montgomery holiday package?
It’s impossible to predict what tomorrow might bring, so it’s comforting to know that you can change or cancel your Montgomery holiday package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for further details.

* 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.