Montclare Vacations from $407

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The Latest Montclare Vacation Packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$407

per person

Nov 26 - Dec 1

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (3,012 reviews)

This is my second time staying here bc it’s so convenient, simple and the staff is great.

Reviewed on Sep 23, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$629

per person

Nov 26 - Dec 1

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (561 reviews)

I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!

Reviewed on Sep 21, 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$987

per person

Nov 9 - Nov 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.6/10 Exceptional! (1,995 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$526

per person

Nov 26 - Dec 1

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,681 reviews)

Clean room, helpful, friendly staff. Plenty of eats and shopping & things to do for kids.

Reviewed on Sep 24, 2026

Stay One Chicago

Downtown Chicago

Save 100% on your flight

$1,104

per person

Nov 26 - Dec 1

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

7.8/10 Good! (12 reviews)

Very nice and clean property. Beds were extremely comfortable and the room was spacious! Loved it!

Reviewed on Sep 20, 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

$171 nightly

$203 total

Oct 25 - Oct 26

Total with taxes and fees

8.8/10 Excellent! (5,435 reviews)

"Elevator was broken, took 15 minutes each time I needed it"

Reviewed on Sep 24, 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$153 nightly

$182 total

Oct 25 - Oct 26

Total with taxes and fees

8/10 Very Good! (10,201 reviews)

"Not well thought or planned for the convenience of the traveler. For example there was way to control the room temperature, sheets were short for tall people"

Reviewed on Sep 24, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$161 nightly

$191 total

Oct 25 - Oct 26

Total with taxes and fees

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.