Cheap Flights to Chesterton from $50
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How Much Does it Cost To Fly To Chesterton?
The cheapest prices found with in the last 7 days for return flights were $101 and $50 for one-way flights to Chesterton for the period specified. Prices and availability are subject to change. Additional terms apply
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$101 Roundtrip, found 4 hours ago
$101
Roundtrip
found 4 hours ago
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$138 Roundtrip, found 14 hours ago
$138
Roundtrip
found 14 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | August 17 to August 24 | $187 |
| LAX | Chicago | September 9 to September 12 | $240 |
| HKG | Chicago | September 3 to October 8 | $877 |
| CAN | Chicago | September 8 to September 12 | $1,045 |
| FCO | Chicago | July 14 to July 15 | $1,046 |
| PVG | Chicago | September 10 to September 16 | $1,177 |
| PEK | Chicago | September 2 to September 30 | $1,189 |
| PVG | Chicago | September 7 to March 3 | $1,196 |
| FOC | Chicago | September 6 to October 4 | $1,319 |
| HKG | Chicago | July 19 to September 26 | $1,319 |
| XIY | Chicago | September 21 to October 18 | $1,403 |
| SZX | Chicago | July 6 to July 10 | $1,478 |
| CTU | Chicago | September 17 to November 8 | $1,629 |
| FOC | Chicago | August 5 to August 26 | $1,629 |
| PEK | Chicago | July 30 to August 1 | $2,577 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | July 3 to July 7 | $342 |
| LAX | Chicago | July 4 to July 12 | $371 |
| LAX | Rockford | July 5 to July 12 | $533 |
| FCO | Chicago | July 5 to July 12 | $727 |
| HKG | Chicago | July 3 to August 10 | $974 |
| CAN | Chicago | July 3 to August 18 | $1,224 |
| PVG | Chicago | July 3 to December 27 | $1,478 |
| PEK | Chicago | July 3 to September 25 | $1,554 |
| PEK | Chicago | July 3 to September 26 | $2,286 |
Chesterton Flight Information
Traveling to | Chesterton |
|---|---|
Lowest Price | $101 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing Chesterton Accommodation Deals
Fairbridge Inn Express Chesterton
713 Plaza Dr. Chesterton IN
$100 nightly
The price is $112 total per night from Jun 29 to Jun 30
$112 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Chesterton. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our ...
6.8/10 (356 reviews)
"We spent 2 nights at this hotel last weekend. The staff (Debbie) was one of the friendliest people I’ve ever met. She had us all laughing from the moment we met her. She was awesome and I would go back to stay there again based on Debbie alone. One thing to note, the fridge wasn’t working when we ..."
Reviewed on Jun 9, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$140 nightly
The price is $157 total per night from Jun 29 to Jun 30
$157 total
Jun 29 - Jun 30
Total with taxes and fees
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,004 reviews)
"SERVICE STAFF IS DOING A GREAT JOB"
Reviewed on Jun 28, 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
$110 nightly
The price is $124 total per night from Jun 29 to Jun 30
$124 total
Jun 29 - Jun 30
Total with taxes and fees
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. ...
8.2/10 Very Good! (1,003 reviews)
"Keycards stopped working. Halls not vacuumed"
Reviewed on Jun 26, 2026
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.
Luxury Hotels in Chesterton
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
$110 nightly
The price is $124 total per night from Jun 29 to Jun 30
$124 total
Jun 29 - Jun 30
Total with taxes and fees
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. ...
8.2/10 Very Good! (1,003 reviews)
"Keycards stopped working. Halls not vacuumed"
Reviewed on Jun 26, 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$106 nightly
The price is $119 total per night from Jul 27 to Jul 28
$119 total
Jul 27 - Jul 28
Total with taxes and fees
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 ...
8/10 Very Good! (765 reviews)
"The property lacked any presentation - just a building and a parking lot. The breakfast was minimal, our room appeared clean, yet the floor felt like it needed swept. Overall, the place was adequate and met our need of an affordable place to sleep."
Reviewed on Jun 27, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$140 nightly
The price is $157 total per night from Jun 29 to Jun 30
$157 total
Jun 29 - Jun 30
Total with taxes and fees
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,004 reviews)
"SERVICE STAFF IS DOING A GREAT JOB"
Reviewed on Jun 28, 2026
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.
Family Friendly Hotels in Chesterton
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$140 nightly
The price is $157 total per night from Jun 29 to Jun 30
$157 total
Jun 29 - Jun 30
Total with taxes and fees
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (1,004 reviews)
"SERVICE STAFF IS DOING A GREAT JOB"
Reviewed on Jun 28, 2026
Hilton Garden Inn Chesterton
501 Gateway Boulevard Chesterton IN
$159 nightly
The price is $178 total per night from Jul 1 to Jul 2
$178 total
Jul 1 - Jul 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chesterton. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
8.8/10 Excellent! (1,000 reviews)
"Clean and well maintained hotel. Convenient items for sale in the lobby and a coffee shop right across the street."
Reviewed on Jun 24, 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$106 nightly
The price is $119 total per night from Jul 27 to Jul 28
$119 total
Jul 27 - Jul 28
Total with taxes and fees
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 ...
8/10 Very Good! (765 reviews)
"The property lacked any presentation - just a building and a parking lot. The breakfast was minimal, our room appeared clean, yet the floor felt like it needed swept. Overall, the place was adequate and met our need of an affordable place to sleep."
Reviewed on Jun 27, 2026
Save an average of 15% on thousands of hotels when you're signed in
Fairbridge Inn Express Chesterton
713 Plaza Dr. Chesterton IN
$100 nightly
The price is $112 total per night from Jun 29 to Jun 30
$112 total
Jun 29 - Jun 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Chesterton. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our ...
6.8/10 (356 reviews)
"We spent 2 nights at this hotel last weekend. The staff (Debbie) was one of the friendliest people I’ve ever met. She had us all laughing from the moment we met her. She was awesome and I would go back to stay there again based on Debbie alone. One thing to note, the fridge wasn’t working when we ..."
Reviewed on Jun 9, 2026
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.
Best Chesterton Flight and Hotel Packages
Chesterton flight + hotel packages - economy flights
Price found within the past 48 hours. Click for updated prices.
Chesterton flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Philadelphia to Chesterton
View all tripsChesterton flight + hotel packages - business class flights
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Los Angeles to Chesterton
View all tripsChesterton flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Special
Schiller Park, Illinois, USA
$14
$63 total
found 1 day ago
Midsize
Schiller Park, Illinois, USA
$15
$65 total
found 1 day ago
Standard
Schiller Park, Illinois, USA
$16
$67 total
found 1 day ago
Compact SUV
Schiller Park, Illinois, USA
$19
$74 total
found 1 day ago
Plane Tickets To Chesterton
Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Chesterton. Browse through our inventory to explore a wide range of cheap flights to Chesterton to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Chesterton as you anxiously await to exit the plane and explore what Chesterton has to offer. Considering all the amazing local food and culture in Chesterton, we won't hold this against you.
When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Chesterton to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Chesterton without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Chesterton with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Chesterton today!
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