Montclare Vacations from $471

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The Latest Montclare Vacation Packages

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

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$471

per person

Nov 11 - Nov 14

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.2/10 Wonderful! (520 reviews)

Location and facility was very nice

Reviewed on Sep 7, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$571

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Breakfast had some cold cuts, but for a vegan there wasn't much more options than your standard US continental. The TV (which turns on automatically every time you enter the room - very annoying) was the worst setup I've seen in a hotel, the connection to cast wasn't working because the TV wasn't connected to wifi, the remote was weird (no volume/channel controls). Lobby was nauseatingly over-fragranced, makes me wonder what horrible scent they're trying to cover up. Tried to use the stairs instead of the slow elevators and couldn't get out on the 2nd floor for breakfast since the stair exits are locked. Overall fair to ok but missing the attention to detail that would've been nice at the price point. I definitely wouldn't stay for business travel.

Reviewed on Sep 9, 2026

The Langham, Chicago

Downtown Chicago

Save 100% on your flight

$1,417

per person

Nov 24 - Nov 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

9.8/10 Exceptional! (1,004 reviews)

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$525

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (165 reviews)

Old,

Reviewed on Sep 8, 2026

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$624

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,512 reviews)

Good proximity to the river and local sights. Property is a little dated and the driveway is always full of cars. Rooms could use a refresh. Shower is very small.

Reviewed on Sep 9, 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

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$151 nightly

$180 total

Sep 10 - Sep 11

Total with taxes and fees

8/10 Very Good! (10,340 reviews)

"Muy buena ubicacion excelente servicios"

Reviewed on Sep 9, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$179 nightly

$213 total

Sep 10 - Sep 11

Total with taxes and fees

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

9.4/10 Exceptional! (891 reviews)

"Great spot!"

Reviewed on Sep 7, 2026

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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.