Montclare Vacations from $501

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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

$501

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.2/10 Very Good! (2,899 reviews)

Level Chicago Fulton Market

Downtown Chicago

$772

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (544 reviews)

The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on Aug 17, 2026

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$829

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

We were blown away that every single person associated with the hotel was kind, helpful, great at their job, accommodating, and basically wonderful. The hotel was amazingly clean, environmentally forward-thinking, safe, and handy to EVERYTHING in downtown Chicago. The best surprise was the massive breakfast buffet that was included in the price of the room. The breakfast accommodated a steady stream of guests and never ran out of the ample variety of food. It was the perfect way to begin each day. Another treat: the rooftop bar and the hotel bar. Excellent service and skilled bar-tenders. It's a gem and don't hesitate to book a room in this hotel.

Reviewed on Aug 19, 2026

Holiday Inn & Suites Chicago - Downtown by IHG

Downtown Chicago

Save 100% on your flight

$522

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,123 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$938

per person

Oct 2 - Oct 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,638 reviews)

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 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 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 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

$130 nightly

$155 total

Sep 9 - Sep 10

Total with taxes and fees

8/10 Very Good! (10,262 reviews)

"The bar was nice. Room felt a little old, only had a tiny old tv, door handles definitely could have been replaced on the bathroom. Good location, close to the museums and nice restaurants. Did not have parking on property but a few lots are nearby."

Reviewed on Aug 19, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Aug 24 - Aug 25

Total with taxes and fees

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

$250 nightly

$294 total

Sep 12 - Sep 13

Total with taxes and fees

See all 4,818 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.