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Find Hotels with Bars in Chesterton, IN

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Check availability on Chesterton Hotels with Bars

Our top choices for Chesterton hotels with a bar

Property entrance
Spring House Inn

Spring House Inn

2.5 star property
Chesterton
9.0 out of 10, Wonderful, (1005)
"Beautiful Hotel"
United States
Joseph
$93 nightly
The price is $105
Dec 10 - Dec 11
Total with taxes and fees
Spring House Inn
Lobby
Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

3.0 star property
Chesterton
8.8 out of 10, Excellent, (1001)
"We loved staying here. "
United States
Linda
$103 nightly
The price is $116
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Chesterton
Exterior
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 star property
Michigan City
8.2 out of 10, Very Good, (1867)
"Great staff, nice room"
United States
Tina Marie
$108 nightly
The price is $121
Jan 1 - Jan 2, 2026
Total with taxes and fees
Blue Chip Casino Hotel and Spa
4 restaurants, dinner served
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 star property
New Buffalo
9.4 out of 10, Exceptional, (1635)
"Great place, hotel room is very well appointed. "
United States
Stuart
$109 nightly
The price is $115
Dec 10 - Dec 11
Total with taxes and fees
Four Winds Casino Resort – New Buffalo
Front of property
The Brewery Lodge Hotel

The Brewery Lodge Hotel

3.5 star property
Michigan City
9.0 out of 10, Wonderful, (788)
"Great place to stay"
United States
James
$124 nightly
The price is $136
Dec 10 - Dec 11
Total with taxes and fees
The Brewery Lodge Hotel
Lobby
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4.0 star property
East Chicago
8.6 out of 10, Excellent, (1008)
"Great stay in clean modern room."
United States
Douglas
$107 nightly
The price is $120
Jan 5 - Jan 6, 2026
Total with taxes and fees
Ameristar Casino Hotel East Chicago
Children's pool
Rodeway Inn

Rodeway Inn

2.5 star property
Portage
7.0 out of 10, Good, (792)
"Clean room, nice staff"
United States
Marcelo
$52 nightly
The price is $58
Dec 16 - Dec 17
Total with taxes and fees
Rodeway Inn
View from property
The Blue Heron Inn

The Blue Heron Inn

3.0 star property
La Porte
8.8 out of 10, Excellent, (500)
"This is a nice family-owned property. They have a nice staff and, though it’s a little dated, it’s clean and comfortable with a nice breakfast."
United States
Laura
$109 nightly
The price is $122
Dec 10 - Dec 11
Total with taxes and fees
The Blue Heron Inn
Indoor pool, seasonal outdoor pool, sun loungers
Pine Lake Resort and Banquets

Pine Lake Resort and Banquets

2.5 star property
La Porte
6.8 out of 10, (582)
"Great stay"
United States
Tiffany
$79 nightly
The price is $91
Dec 10 - Dec 11
Total with taxes and fees
Pine Lake Resort and Banquets
Exterior
Hilton Garden Inn Merrillville

Hilton Garden Inn Merrillville

3.0 star property
Green Acres
8.4 out of 10, Very Good, (1001)
"Front desk was very helpful and friendly hotel room was very clean and quiet"
United States
Rebecca
$103 nightly
The price is $116
Dec 16 - Dec 17
Total with taxes and fees
Hilton Garden Inn Merrillville
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 Chesterton Hotel Reviews

Hilton Garden Inn Chesterton

Hilton Garden Inn Chesterton

10/10 Excellent
"Very clean room Staff friendly "
Jeff 1-night trip
Posted 2 days ago
Hilton Garden Inn Chesterton

Frequently asked questions

Searching for hotels with bars in Chesterton?
Chesterton features 62 hotels and other lodging options to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, consider a visit to Lake Michigan.
What are the best hotels with bars in Chesterton?
Here are some of the top Chesterton properties with bars: Spring House Inn: Enjoy the bar, free breakfast, and free WiFi. Hilton Garden Inn Chesterton: Hotel with restaurant. Enjoy the bar, free parking, and breakfast.
What is there to do in Chesterton?
Delight in the outdoors by visiting Lake Michigan, then check out the local bars and enjoy a refreshing drink. Other places to see include Lustron House and Chellberg Farm. Chesterton is appreciated for its shops and restaurants.
When is the best time to visit Chesterton?
Visiting local bars in Chesterton is better when you know what the weather holds. These temperatures and rainfall averages can help you determine 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 31°F. The snowiest months in Chesterton are January, December, November, and February, with each month seeing an average of 6 inches of snowfall.
How can I get to Chesterton and around the area?
You might want to make the most of these transportation options in and around Chesterton: Fly into Chicago Midway Airport (MDW), which is located 37 mi (59.6 km) away from the city center. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 50.2 mi (80.7 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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