
Deals on vacations and trips to Chesterton
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Chesterton flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

The Chicago Hotel Collection River North
Downtown Chicago
Save 100% on your flight
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A lobby fireplace, express check-out, and luggage storage are also on offer.

The French Country Inn Lake Geneva
Save 100% on your flight
per person
Jul 21 - Jul 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A private beach and a restaurant are featured at this smoke-free hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area, luggage storage, and concierge services are also on offer.

Claridge House
Downtown Chicago
Save 100% on your flight
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. You'll appreciate the gym, bar/lounge, and coffee shop.

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.
Top Chesterton hotels deals

Spring House Inn
303 N Mineral Springs Rd, Chesterton, IN
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $156 total per night
$156 total
Jun 1 - Jun 2
Total includes taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like self-serve breakfast and free self parking.
Pool
Breakfast included

Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20, Chesterton, IN
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $109 total per night
$109 total
Jun 29 - Jun 30
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub

Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $123 total per night
$123 total
Jun 2 - Jun 3
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the sauna and free perks like continental breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a lobby fireplace are also on offer.
Pool
Breakfast included

Waterbird Lakeside Inn
556 Indian Boundary Road, Chesterton, IN
Free Cancellation
Reserve now, pay when you stay
$90 nightly
The price is $101 total per night
$101 total
Jun 1 - Jun 2
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and laundry facilities are also on offer.
Parking included
Free WiFi

Hilton Garden Inn Chesterton
501 Gateway Boulevard, Chesterton, IN
Free Cancellation
Reserve now, pay when you stay
$116 nightly
The price is $129 total per night
$129 total
Jun 15 - Jun 16
Total includes taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 4 conference rooms, 24-hour business center, and express check-out. Enjoy the 24-hour gym and perks like free self parking.
Pool
Pet friendly

Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road, Chesterton, IN
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $93 total per night
$93 total
Jun 25 - Jun 26
Total includes taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.
Breakfast included
Parking included
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.
Popular places to visit

Indiana Dunes State Park
4.5/5(185 reviews)
The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.

Bailly Homestead - American Indians and Fur Traders
4.5/5(3 reviews)
You can find out about the history of Porter with a stop at Bailly Homestead - American Indians and Fur Traders. Wander the beautiful beaches and lakeside in the area.

Waverly Beach
Why not spend a lazy afternoon at Waverly Beach during your trip to Chesterton? Stroll along the beaches or visit the shops in the area.
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