Montclare Vacations from $630

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The Latest Montclare Vacation Packages

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

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Save 100% on your flight

$630

per person

Dec 5 - Dec 12

found 15 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

8.6/10 Excellent! (1,001 reviews)

Room was very clean and Very

Reviewed on Sep 16, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

$1,126

per person

Oct 21 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,174 reviews)

Love the the hotel, great location.

Reviewed on Sep 17, 2026

Swissotel - Chicago

Downtown Chicago

$1,088

per person

Oct 21 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9/10 Wonderful! (3,512 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,222

per person

Oct 21 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,681 reviews)

Be aware of all the hidden changes and you have to ask for housing keeping to clean your room. Stayed 6 days and didn’t get my room cleaned once. No fresh towels, no clean water, and no maid beds. When we brought it up to learn about charges that were made they told us that we should have asked for house keeping to brings towels, etc.

Reviewed on Sep 16, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$670

per person

Oct 21 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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

Can’t complain, everything was perfectly good!

Reviewed on Sep 16, 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

$159 nightly

$190 total

Sep 20 - Sep 21

Total with taxes and fees

8.8/10 Excellent! (5,432 reviews)

"Location is great."

Reviewed on Sep 17, 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

Oct 13 - Oct 14

Total with taxes and fees

8/10 Very Good! (2,249 reviews)

"The room was clean and the bed comfortable but the place is worn and needs some updates. Bedside lamp did not work on right side. Door kept sticking. Water pressure was great but the shower curtain had no magnet or suction to keep it in place. Free coffee was so so. Great location. And both Angela ..."

Reviewed on Sep 17, 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$164 nightly

$195 total

Sep 27 - Sep 28

Total with taxes and fees

8/10 Very Good! (10,263 reviews)

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Reviewed on Sep 16, 2026

See all 4,839 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.