Chesterton flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
per person
Jul. 26 - Jul. 29
found 7 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul. 26 - Jul. 29
found 7 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Jul. 19 - Jul. 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Save 100% on your flight
per person
Jul. 20 - Jul. 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul. 19 - Jul. 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Chesterton hotels deals
Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $179 per night
CA $179
per night
Jun. 17 - Jun. 18
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
Spring House Inn
303 N Mineral Springs Rd, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $136 per night
CA $136
per night
Jun. 17 - Jun. 18
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
Hilton Garden Inn Chesterton
501 Gateway Boulevard, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $191 per night
CA $191
per night
Jun. 30 - Jul. 1
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
Hot tub
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Stay at this cabin in Chesterton. Enjoy free WiFi, an in-room coffeemaker, and housekeeping. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Kitchen
Washer
Waterbird Lakeside Inn
556 Indian Boundary Road, Chesterton, IN
Free cancellation
Reserve now, pay when you stay
The price is CA $151 per night
CA $151
per night
Jun. 25 - Jun. 26
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Parking included
Free WiFi
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 $155 per night
CA $155
per night
Jun. 19 - Jun. 20
Book a stay at this business-friendly hotel in Chesterton. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Indiana Dunes National Park and Indiana Dunes State Park are located nearby.
Pool
Hot tub
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 with a trip to Indiana Dunes State Park, a popular 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.
Photos of local treasures
Browse Chesterton vacation photos for more inspiration