Montclare Vacations from $344
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The Latest Montclare Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $615, price is now $344 per person
$344
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.
Reviewed on Oct 11, 2025
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was $1,473, price is now $537 per person
$537
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.
Reviewed on Oct 2, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,623, price is now $883 per person
$883
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Great staff extremely friendly and helpful.
Reviewed on Oct 15, 2025
Where to stay in Montclare
Find the best Montclare areas and neighborhoods for the activities you enjoy most. Learn more about Montclare
Downtown Chicago
5 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.
Montclare Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (9,409 reviews)
"Check-in staff: did not know if there were vending machine on each floor. Stated bar was getting ready to close (9p) but actually open until midnight. Room: bedspread…not sure when it was last washed:-( no extra blanket in the closet."
Reviewed on Oct 14, 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $100 total per night from Nov 10 to Nov 11
$100 total
Nov 10 - Nov 11
Total with taxes and fees
7.8/10 Good! (2,466 reviews)
"Convenient location with very helpful staff!"
Reviewed on Oct 13, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $169 total per night from Nov 9 to Nov 10
$169 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (3,106 reviews)
"nice hotel"
Reviewed on Oct 15, 2025
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.
Discover the most popular places to visit in Montclare
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.