Find Hotels with Bars in Westchester, IL

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Westchester Hotels with Bars

Top Westchester Hotels with Bars

Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2620)
"Accommodation and great customer serbice!"
United States
Haidee
The price is SAR 241
SAR 349 total
includes taxes & fees
5 Jan - 6 January 2026
Freehand Chicago
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2991)
"Great stay"
Canada
Lorrington Ashford
The price is SAR 428
SAR 612 total
includes taxes & fees
2 Jan - 3 January 2026
Swissotel - Chicago
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2915)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is SAR 359
SAR 527 total
includes taxes & fees
15 Dec - 16 Dec
Hotel Riu Plaza Chicago
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2098)
"Would stay again. "
United States
Montroy
Silversmith Hotel Chicago Downtown
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2944)
"Great location and great staff!!"
United States
lynne
The price is SAR 338
SAR 396 total
includes taxes & fees
1 Jan - 2 January 2026
Aloft Chicago Mag Mile
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
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, (3774)
"Great location "
United States
Carlos
The price is SAR 297
SAR 349 total
includes taxes & fees
18 Dec - 19 Dec
The Whitehall Hotel, BW Premier Collection
Exterior
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3107)
"Very nice staff, beautiful hotel and a clean room"
United States
Tara
The price is SAR 447
SAR 644 total
includes taxes & fees
2 Jan - 3 January 2026
The Royal Sonesta Chicago Downtown
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (4216)
"Great location. "
United States
Rodger
The price is SAR 308
SAR 361 total
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Snack bar
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1454)
"Great stay"
United States
Midalia
The price is SAR 327
SAR 384 total
includes taxes & fees
4 Jan - 5 January 2026
Cambria Hotel Chicago Loop - Theatre District
Terrace/patio
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, (2254)
"Perfect environment and location"
China
YIWEI
The price is SAR 333
SAR 519 total
includes taxes & fees
16 Dec - 17 Dec
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.
View all properties

Top Westchester Hotel Reviews

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"great stay"
james 1-night trip
Posted 18 hours ago
Palmer House a Hilton Hotel

Explore a world of travel with Expedia

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: Palmer House a Hilton Hotel: Hotel with restaurant. Enjoy the bar, full-service spa, and breakfast. Embassy Suites by Hilton Chicago Downtown River North: Hotel with restaurant. Enjoy the bar, free breakfast, and WiFi. Hilton Chicago/Magnificent Mile Suites: Hotel with 2 restaurants. Enjoy the 2 bars, free WiFi, and breakfast. Congress Plaza Hotel: Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast. CitizenM Chicago Downtown: Hotel with restaurant. Enjoy the bar, free WiFi, and 24-hour fitness center.
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.