Cheap Flights to Chesterton from $49
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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 $117 and $49 for one-way flights to Chesterton for the period specified. Prices and availability are subject to change. Additional terms apply
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$117 Roundtrip, just found
$117
Roundtrip
just found
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | August 25 to August 29 | $201 |
| LAX | Chicago | September 9 to September 12 | $240 |
| LAX | Rockford | August 22 to August 26 | $295 |
| FCO | Chicago | September 25 to October 7 | $549 |
| HKG | Chicago | September 12 to September 16 | $880 |
| CAN | Chicago | September 8 to September 12 | $1,046 |
| FCO | Chicago | July 14 to July 15 | $1,046 |
| PVG | Chicago | September 10 to September 16 | $1,177 |
| PVG | Chicago | September 7 to March 3 | $1,198 |
| PEK | Chicago | September 8 to March 3 | $1,214 |
| XIY | Chicago | September 21 to October 18 | $1,403 |
| SZX | Chicago | July 7 to July 11 | $1,436 |
| HKG | Chicago | July 6 to December 26 | $1,627 |
| CTU | Chicago | September 17 to November 8 | $1,629 |
| PEK | Chicago | July 3 to September 26 | $2,191 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | July 4 to July 11 | $342 |
| LAX | Chicago | July 4 to July 8 | $407 |
| LAX | Rockford | July 3 to July 4 | $436 |
| FCO | Chicago | July 5 to July 12 | $727 |
| HKG | Chicago | July 3 to July 27 | $982 |
| PEK | Chicago | July 3 to September 25 | $1,243 |
| CAN | Chicago | July 3 to January 12 | $1,262 |
| PVG | Chicago | July 3 to December 27 | $1,565 |
| PEK | Chicago | July 3 to September 26 | $2,191 |
Chesterton Flight Information
Traveling to | Chesterton |
|---|---|
Lowest Price | $117 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, American 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 28 to Jun 29
$112 total
Jun 28 - Jun 29
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 28 to Jun 29
$157 total
Jun 28 - Jun 29
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! (1,002 reviews)
"The room was nice. Our balcony had no chairs like all the other rooms. There was a nice pond at the back of the property. The hotel is a bit tricky to find since it's tucked by the pond."
Reviewed on Jun 26, 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
$110 nightly
The price is $124 total per night from Jun 28 to Jun 29
$124 total
Jun 28 - Jun 29
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! (1,001 reviews)
"The person checking us in was very pleasant and informative. However, the room definitively needed updating. There were places on the walls that had been primed but not painted and paint on the molding around the bathroom door. The view of the lake from the balcony was nice."
Reviewed on Jun 23, 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 28 to Jun 29
$124 total
Jun 28 - Jun 29
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! (1,001 reviews)
"The person checking us in was very pleasant and informative. However, the room definitively needed updating. There were places on the walls that had been primed but not painted and paint on the molding around the bathroom door. The view of the lake from the balcony was nice."
Reviewed on Jun 23, 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 26 to Jul 27
$119 total
Jul 26 - Jul 27
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! (762 reviews)
"Overnight stay on way to Chicago,it was close to freeway, quick check in, free breakfast and room was reasonable . Overall good for the price"
Reviewed on Jun 24, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$140 nightly
The price is $157 total per night from Jun 28 to Jun 29
$157 total
Jun 28 - Jun 29
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! (1,002 reviews)
"The room was nice. Our balcony had no chairs like all the other rooms. There was a nice pond at the back of the property. The hotel is a bit tricky to find since it's tucked by the pond."
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.
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 28 to Jun 29
$157 total
Jun 28 - Jun 29
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! (1,002 reviews)
"The room was nice. Our balcony had no chairs like all the other rooms. There was a nice pond at the back of the property. The hotel is a bit tricky to find since it's tucked by the pond."
Reviewed on Jun 26, 2026
Hilton Garden Inn Chesterton
501 Gateway Boulevard Chesterton IN
$155 nightly
The price is $174 total per night from Jun 28 to Jun 29
$174 total
Jun 28 - Jun 29
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! (1,003 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 26 to Jul 27
$119 total
Jul 26 - Jul 27
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! (762 reviews)
"Overnight stay on way to Chicago,it was close to freeway, quick check in, free breakfast and room was reasonable . Overall good for the price"
Reviewed on Jun 24, 2026
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Fairbridge Inn Express Chesterton
713 Plaza Dr. Chesterton IN
$100 nightly
The price is $112 total per night from Jun 28 to Jun 29
$112 total
Jun 28 - Jun 29
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 - first 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 Charlotte to Chesterton
View all tripsNeed a Car For After Your Flight?
Special
SCHILLER PARK, USA
$4
$38 total
found 4 hours ago
Midsize
Schiller Park, Illinois, USA
$8
$47 total
found 4 hours ago
Standard
Schiller Park, Illinois, USA
$8
$47 total
found 4 hours ago
Compact SUV
Schiller Park, Illinois, USA
$9
$49 total
found 4 hours ago
Lowest prices found within the past 4 hours. Prices and availability subject to change. Additional terms may apply.
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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