Chesterton flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston
per person
Mar. 13 - Mar. 16
found 2 days ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clark Street Beach and Halim Time & Glass Museum are located nearby.
Swissotel - Chicago
Downtown Chicago
per person
Jan. 27 - Jan. 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
W Chicago - Lakeshore
Downtown Chicago
per person
Feb. 10 - Feb. 15
found 22 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
Level Chicago - River North
Downtown Chicago
per person
Mar. 5 - Mar. 9
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Chesterton hotels deals
Spring House Inn
303 N Mineral Springs Rd, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $128 per night
CA $128
CA $143 total
includes taxes & fees
23 Dec - 24 Dec
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Bailly Homestead - American Indians and Fur Traders are located nearby.
Pool
Breakfast included
Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $122 per night
CA $122
CA $137 total
includes taxes & fees
29 Dec - 30 Dec
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Indiana Dunes National Park and Lustron House are located nearby.
Pool
Breakfast included
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
The price is CA $258 per night
CA $258
CA $421 total
includes taxes & fees
6 Jan - 7 Jan 2025
Stay at this cabin in Chesterton. Enjoy free WiFi, patios, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. Popular attractions Indiana Dunes National Park and East Beach are located nearby.
Hilton Garden Inn Chesterton
501 Gateway Boulevard, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $176 total
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this 3-star business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Coffee Creek Watershed Conservancy Preserve are located nearby.
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $122 per night
CA $122
CA $137 total
includes taxes & fees
12 Jan - 13 Jan 2025
Book a stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Bailly Homestead - American Indians and Fur Traders are located nearby.
Pool
Hot tub
Waterbird Lakeside Inn
556 Indian Boundary Road, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $116 per night
CA $116
CA $130 total
includes taxes & fees
23 Dec - 24 Dec
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Lustron House are located nearby.
Parking included
Free WiFi
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(1 review)
Explore the great outdoors at Indiana Dunes State Park, a lovely green space in Chesterton. Wander the beautiful beaches and lakeside in the area.
Bailly Homestead - American Indians and Fur Traders
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.
Frequently asked questions
Photos of local treasures
Browse Chesterton vacation photos for more inspiration