Cheap Flights to Chesterton from $29
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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 $56 and $29 for one-way flights to Chesterton for the period specified. Prices and availability are subject to change. Additional terms apply
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 5 days ago
$56
Roundtrip
found 5 days ago
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$57 Roundtrip, found 2 days ago
$57
Roundtrip
found 2 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | April 14 to April 25 | $136 |
| LAX | Chicago | April 24 to April 28 | $210 |
| LAX | Rockford | April 29 to May 2 | $231 |
| FCO | Chicago | April 17 to April 24 | $557 |
| HKG | Chicago | May 23 to July 15 | $783 |
| CAN | Chicago | May 28 to October 2 | $833 |
| PVG | Chicago | April 15 to May 6 | $1,003 |
| FOC | Chicago | May 11 to July 31 | $1,064 |
| PEK | Chicago | June 16 to September 30 | $1,074 |
| SZX | Chicago | June 2 to November 28 | $1,266 |
| PVG | Chicago | June 15 to June 19 | $1,337 |
| CTU | Chicago | May 1 to May 16 | $1,362 |
| XIY | Chicago | May 15 to May 30 | $1,734 |
| HKG | Chicago | April 1 to May 19 | $3,301 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | March 21 to March 24 | $458 |
| LAX | Rockford | March 21 to March 30 | $568 |
| LAX | Chicago | March 20 to March 22 | $572 |
| FCO | Chicago | March 21 to March 28 | $1,117 |
| HKG | Chicago | March 22 to March 29 | $1,243 |
| PVG | Chicago | March 22 to March 23 | $1,307 |
| PEK | Chicago | March 22 to March 23 | $1,726 |
| SZX | Chicago | March 22 to March 26 | $1,777 |
Chesterton Flight Information
Traveling to | Chesterton |
|---|---|
Lowest Price | $56 |
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
$82 nightly
The price is $92 total per night from Mar 14 to Mar 15
$92 total
Mar 14 - Mar 15
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 (345 reviews)
It's my go to when, I want to get away.
Reviewed on Feb 8, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$84 nightly
The price is $94 total per night from Mar 16 to Mar 17
$94 total
Mar 16 - Mar 17
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)
Great location and staff
Reviewed on Mar 13, 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
$81 nightly
The price is $91 total per night from Mar 16 to Mar 17
$91 total
Mar 16 - Mar 17
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! (1,000 reviews)
We were pleasantly surprised by our room. The floors were clean. The bed was clean. Everything smelled good even in the hallway. There were no noisy neighbors and the balcony overlooking the water was peaceful and beautiful. We loved getting visits from the geese and the beautiful swan. I would absolutely ...
Reviewed on Mar 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.
Luxury Hotels in Chesterton
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
$81 nightly
The price is $91 total per night from Mar 16 to Mar 17
$91 total
Mar 16 - Mar 17
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! (1,000 reviews)
We were pleasantly surprised by our room. The floors were clean. The bed was clean. Everything smelled good even in the hallway. There were no noisy neighbors and the balcony overlooking the water was peaceful and beautiful. We loved getting visits from the geese and the beautiful swan. I would absolutely ...
Reviewed on Mar 9, 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$78 nightly
The price is $87 total per night from Apr 7 to Apr 8
$87 total
Apr 7 - Apr 8
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! (734 reviews)
Room was clean staff was great.
Reviewed on Feb 25, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$84 nightly
The price is $94 total per night from Mar 16 to Mar 17
$94 total
Mar 16 - Mar 17
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)
Great location and staff
Reviewed on Mar 13, 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
$84 nightly
The price is $94 total per night from Mar 16 to Mar 17
$94 total
Mar 16 - Mar 17
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)
Great location and staff
Reviewed on Mar 13, 2026
Hilton Garden Inn Chesterton
501 Gateway Boulevard Chesterton IN
$108 nightly
The price is $121 total per night from Mar 22 to Mar 23
$121 total
Mar 22 - Mar 23
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! (1,001 reviews)
T
Reviewed on Mar 9, 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$78 nightly
The price is $87 total per night from Apr 7 to Apr 8
$87 total
Apr 7 - Apr 8
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! (734 reviews)
Room was clean staff was great.
Reviewed on Feb 25, 2026
Save an average of 15% on thousands of hotels when you're signed in
Fairbridge Inn Express Chesterton
713 Plaza Dr. Chesterton IN
$82 nightly
The price is $92 total per night from Mar 14 to Mar 15
$92 total
Mar 14 - Mar 15
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 (345 reviews)
It's my go to when, I want to get away.
Reviewed on Feb 8, 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.
Need a Car For After Your Flight?
Special
Schiller Park, Illinois, USA
$8
$47 total
found 8 hours ago
Midsize SUV
Schiller Park, Illinois, USA
$12
$56 total
found 5 hours ago
Standard
Schiller Park, Illinois, USA
$13
$61 total
found 8 hours ago
Compact SUV
Schiller Park, Illinois, USA
$13
$59 total
found 5 hours ago
Lowest prices found within the past 8 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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