Cheap Flights to Chesterton from $27
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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 $54 and $27 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
ORD
O'Hare Intl.
$54 Roundtrip, just found
$54
Roundtrip
just found
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | March 16 to March 25 | $128 |
| LAX | Chicago | February 19 to February 24 | $166 |
| LAX | Rockford | March 11 to March 17 | $244 |
| FCO | Chicago | February 20 to February 27 | $467 |
| FCO | Chicago | February 16 to February 28 | $766 |
| HKG | Chicago | February 10 to July 15 | $858 |
| PEK | Chicago | May 2 to May 16 | $926 |
| CAN | Chicago | April 1 to April 29 | $934 |
| PVG | Chicago | March 16 to March 31 | $955 |
| HKG | Chicago | April 15 to July 8 | $1,024 |
| FOC | Chicago | February 19 to June 23 | $1,147 |
| XIY | Chicago | April 10 to September 19 | $1,153 |
| SZX | Chicago | February 3 to February 7 | $1,172 |
| PVG | Chicago | March 6 to March 12 | $1,197 |
| PEK | Chicago | March 7 to August 7 | $1,397 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | January 31 to February 1 | $260 |
| LAX | Chicago | January 30 to February 2 | $301 |
| FCO | Chicago | February 1 to February 17 | $598 |
| LAX | Rockford | February 1 to February 2 | $823 |
| HKG | Chicago | January 31 to April 1 | $891 |
| PVG | Chicago | January 31 to March 29 | $1,102 |
| CAN | Chicago | February 1 to February 5 | $1,162 |
| PEK | Chicago | January 31 to April 18 | $1,226 |
| XIY | Chicago | February 1 to July 1 | $1,546 |
Chesterton Flight Information
Traveling to | Chesterton |
|---|---|
Lowest Price | $54 |
Number of Airlines Serving | |
Airlines Serving | Spirit Airlines, 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
$80 nightly
The price is $90 total per night from Jan 26 to Jan 27
$90 total
Jan 26 - Jan 27
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 (344 reviews)
Everything work properly and plenty of amenities nearby
Reviewed on Jan 20, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$89 nightly
The price is $100 total per night from Jan 31 to Feb 1
$100 total
Jan 31 - Feb 1
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 ...
8.4/10 Very Good! (1,000 reviews)
Friendly staff, clean and comfy
Reviewed on Jan 10, 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
$76 nightly
The price is $86 total per night from Jan 26 to Jan 27
$86 total
Jan 26 - Jan 27
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. ...
8/10 Very Good! (995 reviews)
Staff really nice. Room clean and better than expected. Nice layout and large rooms.
Reviewed on Jan 19, 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
$76 nightly
The price is $86 total per night from Jan 26 to Jan 27
$86 total
Jan 26 - Jan 27
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. ...
8/10 Very Good! (995 reviews)
Staff really nice. Room clean and better than expected. Nice layout and large rooms.
Reviewed on Jan 19, 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$72 nightly
The price is $81 total per night from Feb 15 to Feb 16
$81 total
Feb 15 - Feb 16
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! (720 reviews)
Good stay
Reviewed on Dec 21, 2025
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$89 nightly
The price is $100 total per night from Jan 31 to Feb 1
$100 total
Jan 31 - Feb 1
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 ...
8.4/10 Very Good! (1,000 reviews)
Friendly staff, clean and comfy
Reviewed on Jan 10, 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
$89 nightly
The price is $100 total per night from Jan 31 to Feb 1
$100 total
Jan 31 - Feb 1
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 ...
8.4/10 Very Good! (1,000 reviews)
Friendly staff, clean and comfy
Reviewed on Jan 10, 2026
Hilton Garden Inn Chesterton
501 Gateway Boulevard Chesterton IN
$98 nightly
The price is $109 total per night from Feb 1 to Feb 2
$109 total
Feb 1 - Feb 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 ...
8.6/10 Excellent! (1,002 reviews)
Everything was great, like always
Reviewed on Jan 19, 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$72 nightly
The price is $81 total per night from Feb 15 to Feb 16
$81 total
Feb 15 - Feb 16
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! (720 reviews)
Good stay
Reviewed on Dec 21, 2025
Save an average of 15% on thousands of hotels when you're signed in
Fairbridge Inn Express Chesterton
713 Plaza Dr. Chesterton IN
$80 nightly
The price is $90 total per night from Jan 26 to Jan 27
$90 total
Jan 26 - Jan 27
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 (344 reviews)
Everything work properly and plenty of amenities nearby
Reviewed on Jan 20, 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
$3
$35 total
found 1 day ago
Midsize
Schiller Park, Illinois, USA
$4
$37 total
found 1 day ago
Standard
Schiller Park, Illinois, USA
$4
$38 total
found 1 day ago
Compact SUV
Schiller Park, Illinois, USA
$5
$41 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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