Find Hotels with Bars in Winnetka, IL

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Our top choices for Winnetka 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, (2642)
"The room was spotless and the staff where great!"
United States
Maria
$65 nightly
The price is $77
Jan 4 - Jan 5, 2026
Total with taxes and fees
Freehand Chicago
Lobby
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2961)
"Great location and great staff!!"
United States
lynne
$79 nightly
The price is $93
Jan 14 - Jan 15, 2026
Total with taxes and fees
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, (2977)
"Excellent stay great location and great rooms"
United States
Joseph
$124 nightly
The price is $145
Dec 21 - Dec 22
Total with taxes and fees
Hotel Riu Plaza 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
$123 nightly
The price is $144
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hyatt Centric Chicago Magnificent Mile
Exterior
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (3013)
"Enjoyed this hotel stay. "
United States
Kimberly
$88 nightly
The price is $104
Dec 21 - Dec 22
Total with taxes and fees
Warwick Allerton - 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, (2261)
"This place was amazing !"
United States
Jayla Danyell
$121 nightly
The price is $142
Dec 23 - Dec 24
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
Bar (on property)
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, (3795)
"Comfortable Room, great location and Excellent Staff. "
United States
Charles
$83 nightly
The price is $97
Dec 21 - Dec 22
Total with taxes and fees
The Whitehall Hotel, BW Premier Collection
Property amenity
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1459)
"Clean, modern, friendly/helpful staff, the perfect spot for staying for a show at The Chicago Theatre. Parking was close and easy too. "
United States
Megan
$87 nightly
The price is $102
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cambria Hotel Chicago Loop - Theatre District
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1756)
"Clean and staff was courteous. "
United States
HANNAH
$71 nightly
The price is $84
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hilton Garden Inn Chicago Downtown South Loop
Lobby sitting area
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (1787)
"Great stay in a great area."
United States
Giselle
$75 nightly
The price is $88
Dec 17 - Dec 18
Total with taxes and fees
Hotel Saint Clair- Magnificent Mile
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 Winnetka Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Lovely hotel/staff"
Isaiah 3-night trip
Posted 2 hours ago
Crowne Plaza Chicago West Loop by IHG

Frequently asked questions

Searching for hotels with bars in Winnetka?
Let Expedia help you find the perfect hotel in Winnetka or in the larger area that has a bar where you can enjoy a late-night cocktail. While you're here, you can check out Lake Michigan.
What are the best hotels with bars in Winnetka?
Here are a few of the top hotels with bars in and around Winnetka: 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 restaurant. Enjoy the bar, full-service spa, and breakfast. Palmer House a Hilton Hotel: Enjoy the bar, free WiFi, and breakfast. Club Quarters Hotel Wacker at Michigan, Chicago: Hotel with restaurant. Enjoy the bar, free WiFi, and 24-hour fitness center. Silversmith Hotel Chicago Downtown: Hotel with restaurant. Enjoy the bar, free WiFi, and breakfast.
What is there to do in Winnetka?
Absorb the local culture in the area by visiting Wrigley Field and United Center, then unwind with a refreshing drink. Other places to see include Lake Michigan.
When is the best time to visit Winnetka?
Visiting local bars in Winnetka is better when you know what the weather holds. These temperatures and rainfall averages can help you choose the best time for bar hopping. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Winnetka is 48 inches.
How can I get to Winnetka and around the area?
You might want to make the most of these transportation options in and around Winnetka: Fly into Chicago, IL (PWK-Chicago Executive), which is located 8.4 mi (13.5 km) from the city center. Otherwise, look for flights into Chicago O'Hare Intl. Airport (ORD), which is 12.5 mi (20.2 km) away. To explore the surrounding area, hop aboard a train at Winnetka Station or Winnetka Indian Hill Station.

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