Montclare Vacations from $408

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Montclare Vacation Packages

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

Chicago Marriott Southwest at Burr Ridge

Save 100% on your flight

$408

per person

Nov 12 - Nov 16

found 14 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.8/10 Excellent! (1,004 reviews)

Kimpton Gray Hotel by IHG

Downtown Chicago

Save 100% on your flight

$466

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,007 reviews)

Stayed one night on a quick trip for a show. We are regular travelers to Chicago. The hotel is in a wonderful historic building, really interesting 2nd floor lobby and sitting area. The lounge was closed on Sunday's so we missed it but it looked very nice. The hotel lobby offered a 5-6pm happy hour with wine and beer. The room was very nice and good size for Chicago. Not brand new, but still in good condition and clean. The bed was comfortable, the room was quiet. Kimpton hotels are usually great and this one was up to standard.

Reviewed on Sep 30, 2026

The Peninsula Chicago

Downtown Chicago

Save 100% on your flight

$1,224

per person

Nov 22 - Nov 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.8/10 Exceptional! (1,010 reviews)

It is the greatest will be there again

Reviewed on Sep 29, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$556

per person

Dec 2 - Dec 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (573 reviews)

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$500

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (527 reviews)

The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.

Reviewed on Sep 27, 2026

Where to stay in Montclare

Find the best Montclare areas and neighborhoods for the activities you enjoy most. Learn more about Montclare

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Montclare Hotel Deals

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$167 nightly

$199 total

Nov 1 - Nov 2

Total with taxes and fees

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$125 nightly

$149 total

Nov 1 - Nov 2

Total with taxes and fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Nov 1 - Nov 2

Total with taxes and fees

8/10 Very Good! (2,385 reviews)

"Second time at this property. Short stay but easy to get to and fit our needs perfectly."

Reviewed on Oct 1, 2026

See all 4,851 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.