Find Hotels with Bars in Westchester, IL

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Check availability on Westchester Hotels with Bars

Our top choices for Westchester hotels with a bar

Cocktail bar
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2651)
"It's an excellent place."
United States
Jose
The price is NT$1,845
NT$2,721 total
includes taxes & fees
Jan 19 - 2026/1/20
Freehand Chicago
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2953)
"The room was very clean, the location was excellent."
United States
Craig
The price is NT$2,491
NT$2,925 total
includes taxes & fees
Jan 15 - 2026/1/16
Aloft Chicago Mag Mile
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2991)
"Excellent stay great location and great rooms"
United States
Joseph
The price is NT$2,856
NT$4,241 total
includes taxes & fees
Dec 21 - Dec 22
Hotel Riu Plaza Chicago
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2999)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is NT$1,965
NT$3,232 total
includes taxes & fees
Jan 13 - 2026/1/14
Warwick Allerton - Chicago
American cuisine, alfresco dining
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1933)
"The room was nice, the area was perfect for walking distance for food and activities. "
United States
Alexis
The price is NT$2,630
NT$3,828 total
includes taxes & fees
Jan 10 - 2026/1/11
The Godfrey Hotel Chicago
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1053)
"Perfect location to surrounding area and activities, friendly staff, clean rooms, amazing gym, and delicious food."
United States
Hannah
The price is NT$3,091
NT$4,554 total
includes taxes & fees
Jan 7 - 2026/1/8
Hyatt Centric Chicago Magnificent Mile
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Downtown Chicago
8.2 out of 10, Very Good, (3786)
"Clean room, good location, friendly staff"
United States
Zacharias
The price is NT$2,414
NT$2,834 total
includes taxes & fees
Jan 6 - 2026/1/7
The Whitehall Hotel, BW Premier Collection
Exterior
Hilton Chicago

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2383)
"Great amenities and staff"
United States
Edward J
The price is NT$3,594
NT$5,145 total
includes taxes & fees
Dec 27 - Dec 28
Hilton Chicago
Lobby
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2002)
"Great location, clean hotel"
United States
Andre
The price is NT$2,776
NT$3,999 total
includes taxes & fees
Jan 2 - 2026/1/3
Millennium Knickerbocker Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2268)
"Great staff and restaurants!!"
United States
Abigale
The price is NT$2,870
NT$4,443 total
includes taxes & fees
Jan 15 - 2026/1/16
Sable at Navy Pier Chicago, Curio Collection by Hilton
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.
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Top Westchester Hotel Reviews

Frequently asked questions

Searching for hotels with bars in Westchester?
Though you might not find a hotel in Westchester well-known for its bar, you will find 10 properties to choose from, some of which will have an onsite bar where you can unwind with an evening cocktail after sightseeing. While you're in the area, consider a visit to Wrigley Field and Michigan Avenue.
What are the best hotels with bars in Westchester?
Here are some favorite hotels with bars in and around Westchester: Embassy Suites by Hilton Chicago Downtown River North: Hotel with restaurant. Enjoy the bar, free breakfast, and WiFi. Hilton Chicago/Magnificent Mile Suites: Enjoy the bar, free WiFi, and breakfast. Silversmith Hotel Chicago Downtown: Hotel with restaurant. Enjoy the bar, full-service spa, and breakfast. Palmer House a Hilton Hotel: Hotel with restaurant. Enjoy the bar, free WiFi, and 24-hour fitness center. Eurostars Magnificent Mile: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi.
What is there to do in Westchester?
Absorb the local culture by visiting Wrigley Field, United Center, and Soldier Field, then unwind with a refreshing drink. Other places to see in the area include Michigan Avenue and Navy Pier. Westchester is known for its shops and restaurants.
When is the best time to visit Westchester?
Visiting local bars in Westchester is more fun in good weather. These rainfall averages and temperatures can help you choose the best time for bar hopping. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
How can I get to Westchester and around the area?
You might want to make the most of these transportation choices in and around Westchester: Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) from the city center. You can also search for flights into Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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