Book Exclusive Chesterton Vacation Packages
Chesterton flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Chicago River Side Suites
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 28
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, daily housekeeping, and slippers. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 11 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park 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 $178 per night
CA $178
CA $200 total
includes taxes & fees
May 30 - May 31
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 Indiana Dunes State Park 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 $129 per night
CA $129
CA $145 total
includes taxes & fees
Jun 4 - Jun 5
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 Indiana Dunes State Park are located nearby.
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
The price is CA $135 per night
CA $135
CA $151 total
includes taxes & fees
Jun 29 - Jun 30
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 Indiana Dunes State Park 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 $124 per night
CA $124
CA $139 total
includes taxes & fees
Jun 1 - Jun 2
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 Indiana Dunes State Park are located nearby.
Parking included
Free WiFi
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $115 per night
CA $115
CA $129 total
includes taxes & fees
Jun 25 - Jun 26
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 Indiana Dunes State Park are located nearby.
Breakfast included
Parking included
Hilton Garden Inn Chesterton
501 Gateway Boulevard, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $162 per night
CA $162
CA $181 total
includes taxes & fees
Jun 15 - Jun 16
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 Indiana Dunes State Park are located nearby.
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
4/5(1 review)
You can take time to visit Indiana Dunes State Park during your travels to 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.
Photos of local treasures
Browse Chesterton vacation photos for more inspiration
