Montclare Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Montclare

Price found within the past 48 hours. Click for updated prices.
La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $988, price is now CA $727 per person
CA $727
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,703, price is now CA $1,160 per person
CA $1,160
per person
Apr 14 - Apr 19
found 4 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Amazing hotel. Always stay here when I make a trip to Chicago.

Reviewed on Feb 10, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,129, price is now CA $790 per person
CA $790
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, staff was so polite and kind and very helpful. We took our 3 year old daughter with us and they were kind to her and welcoming! (That means a lot - not all hotels are welcoming to small children.) they made sure to open the doors for us each time we came in with our stroller. We will absolutely be back to the Riu in Chicago! 10/10

Reviewed on Feb 9, 2026

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Price was CA $1,042, price is now CA $764 per person
CA $764
per person
Mar 31 - Apr 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Staff was great but next to fire station. Beware very noisy if staying city view

Reviewed on Feb 8, 2026

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,478, price is now CA $1,085 per person
CA $1,085
per person
Apr 16 - Apr 21
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,034 reviews)
All good. bar staff was not that friendlly

Reviewed on Feb 3, 2026

Where to stay in Montclare

Find the best Montclare areas and neighborhoods for the activities you enjoy most. Learn more about Montclare
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Montclare Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Feb 11 to Feb 12
CA $122
CA $143 total
Feb 11 - Feb 12
includes taxes & fees
8/10 Very Good! (9,863 reviews)
Good location for many activities. Room was good but less than great.

Reviewed on Feb 7, 2026

Congress Plaza Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $266 per night from Mar 7 to Mar 8
CA $266
CA $312 total
Mar 7 - Mar 8
includes taxes & fees
8.2/10 Very Good! (2,215 reviews)
A very good value. A bit worn, great bed but half the price of the Westin Denver airport.

Reviewed on Feb 8, 2026

Hilton Chicago O'Hare Airport
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Feb 22 to Feb 23
CA $139
CA $163 total
Feb 22 - Feb 23
includes taxes & fees
8.4/10 Very Good! (5,637 reviews)
Yes room was spotless

Reviewed on Feb 4, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,078 properties in Montclare
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.
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All Inclusive Vacations
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Frequently asked questions

How much does a Montclare vacation package cost?
Live it up in Montclare from as low as CA $727. Choose from a great selection of flights, hotels and rental cars to suit your budget. Pick up even more discounts when you add some tours or activities to your package.
How do I get a cheap travel package to Montclare?
Our Montclare vacation packages mean plenty of savings for the savvy traveler. For the best deal, simply combine your flights, hotels and tours into a budget-friendly package. But impressive bargains are just the beginning of your next unforgettable adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 properties throughout the world to choose from. No matter your budget or style, there's a package that's perfect for you.
Where should I stay in Montclare?
With fascinating attractions like Portage Park and Six Corners in this area, look for a hotel located near either one. Community First Medical Center is another sight in Montclare that people flock to.
How far in advance should I book my Montclare vacation?
It can be difficult to know when is the ideal time to book your Montclare vacation. But generally the earlier you book, the more affordable the prices. Sometimes, you can book your flights and hotels nearly a year before departure. If you're considering a last-minute getaway, no need to worry! There are incredible bargains posted on Expedia every day.
What does an Expedia Montclare travel package include?
It comes down to what you're after. If you're traveling solo, you might decide to combine hotels and flights. Bringing the whole family to Montclare? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking a Montclare travel package?
Bundling your bookings into a Montclare vacation package is the most convenient way to organize your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Montclare Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you sure can! Simply choose your preferred air carrier and put together the perfect Montclare trip.
If I'm not able to travel, can I cancel my Montclare vacation package?
If your travel plans in Montclare have changed, it's comforting to know that it's possible to cancel your booking. If you made your booking in the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose fees. For more information, visit our Customer Service Portal.

Discover the most popular places to visit in Montclare

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $46
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.