
Deals on vacations and trips to Chesterton
Save when you book Chesterton package deals

Chesterton flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $477, price is now $274 per person
$274
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $760, price is now $409 per person
$409
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

JW Marriott Chicago
Downtown Chicago
Save 100% on your flight
Price was $811, price is now $491 per person
$491
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $642, price is now $396 per person
$396
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

La Banque Hotel
Save 100% on your flight
Price was $642, price is now $397 per person
$397
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.
Top Chesterton hotels deals

Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20 Chesterton IN
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Feb 25 - Feb 26
Total with 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

Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Free Cancellation
Reserve now, pay when you stay
$83 nightly
The price is $93 total per night
$93 total
Feb 5 - Feb 6
Total with 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

Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $86 total per night
$86 total
Feb 5 - Feb 6
Total with 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

Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $95 total per night
$95 total
Feb 10 - Feb 11
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Enjoy the sauna and perks like free self parking and free WiFi. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.
Pool
Breakfast included

Hilton Garden Inn Chesterton
501 Gateway Boulevard Chesterton IN
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $111 total per night
$111 total
Feb 22 - Feb 23
Total with 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
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
The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.

Indiana Dunes Visitor Center
Explore the great outdoors at Indiana Dunes Visitor Center, a lovely green space in Porter. Wander the beaches and forest in this family-friendly area.

Coffee Creek Watershed Conservancy Preserve
Explore the great outdoors at Coffee Creek Watershed Conservancy Preserve, a lovely green space in Chesterton. Wander the area's beautiful beaches or simply enjoy one of its charming coffeehouses.
Frequently asked questions
Photos of local treasures
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