Cheap Flights to Chesterton from $28
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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 $58 and $28 for one-way flights to Chesterton for the period specified. Prices and availability are subject to change. Additional terms apply
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | June 30 to July 3 | $166 |
| LAX | Chicago | May 12 to May 19 | $215 |
| LAX | Rockford | May 23 to May 27 | $225 |
| FCO | Chicago | May 12 to May 25 | $645 |
| FCO | Chicago | May 30 to June 9 | $941 |
| PEK | Chicago | May 19 to November 6 | $1,020 |
| HKG | Chicago | June 12 to September 30 | $1,056 |
| CAN | Chicago | May 9 to July 19 | $1,094 |
| PVG | Chicago | June 18 to August 7 | $1,258 |
| FOC | Chicago | June 3 to July 30 | $1,427 |
| XIY | Chicago | May 21 to July 23 | $1,434 |
| CTU | Chicago | May 25 to October 26 | $1,661 |
| CAN | Chicago | May 9 to July 19 | $1,725 |
| HKG | Chicago | May 6 to May 10 | $1,852 |
| PEK | Chicago | June 23 to June 28 | $1,951 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | April 25 to May 1 | $333 |
| LAX | Chicago | April 26 to April 30 | $392 |
| LAX | Rockford | April 24 to April 28 | $506 |
| FCO | Chicago | April 24 to May 7 | $919 |
| HKG | Chicago | April 24 to September 24 | $1,333 |
| FOC | Chicago | April 26 to August 10 | $1,660 |
| PVG | Chicago | April 25 to April 28 | $1,786 |
| CAN | Chicago | April 25 to May 6 | $2,000 |
| PEK | Chicago | April 25 to May 5 | $2,068 |
| CTU | Chicago | April 24 to April 25 | $2,263 |
Chesterton Flight Information
Traveling to | Chesterton |
|---|---|
Lowest Price | $58 |
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
$71 nightly
The price is $80 total per night from Apr 24 to Apr 25
$80 total
Apr 24 - Apr 25
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 (347 reviews)
Air/heat unit didn’t work. Had to return to front desk multiple times as key card would stop working. Night Front desk staff was dismissive and acted agitated when asked questions.
Reviewed on Apr 19, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$93 nightly
The price is $105 total per night from Apr 28 to Apr 29
$105 total
Apr 28 - Apr 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! (1,005 reviews)
Great property and amazing rooms
Reviewed on Apr 22, 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
$81 nightly
The price is $91 total per night from Apr 23 to Apr 24
$91 total
Apr 23 - Apr 24
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)
A basic hotel with a beautiful view of a lake full of wildlife. The Waterbird does not offer a lot amenities but it is clean and there are plenty of places to eat nearby. It is near the Dunelands and a good stage to run into Chicago. Bring binoculars for the birds.
Reviewed on Apr 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.
Luxury Hotels in Chesterton
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
$81 nightly
The price is $91 total per night from Apr 23 to Apr 24
$91 total
Apr 23 - Apr 24
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)
A basic hotel with a beautiful view of a lake full of wildlife. The Waterbird does not offer a lot amenities but it is clean and there are plenty of places to eat nearby. It is near the Dunelands and a good stage to run into Chicago. Bring binoculars for the birds.
Reviewed on Apr 20, 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$84 nightly
The price is $94 total per night from May 21 to May 22
$94 total
May 21 - May 22
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! (741 reviews)
Not much for breakfast
Reviewed on Apr 19, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$93 nightly
The price is $105 total per night from Apr 28 to Apr 29
$105 total
Apr 28 - Apr 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! (1,005 reviews)
Great property and amazing rooms
Reviewed on Apr 22, 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
$93 nightly
The price is $105 total per night from Apr 28 to Apr 29
$105 total
Apr 28 - Apr 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! (1,005 reviews)
Great property and amazing rooms
Reviewed on Apr 22, 2026
Hilton Garden Inn Chesterton
501 Gateway Boulevard Chesterton IN
$120 nightly
The price is $134 total per night from May 3 to May 4
$134 total
May 3 - May 4
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! (1,007 reviews)
On site restaurant and bar were convenient and very nice. Walkable to restaurants. Very close to Indiana Dunes. Good WiFi. Clean. Hot tub and pool missed the mark in my opinion. Pool was rather chilly and hot tub doesn’t have bubbles. Maintenance said the tub is a spa so doesn’t have to.
Reviewed on Apr 21, 2026
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$84 nightly
The price is $94 total per night from May 21 to May 22
$94 total
May 21 - May 22
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! (741 reviews)
Not much for breakfast
Reviewed on Apr 19, 2026
Save an average of 15% on thousands of hotels when you're signed in
Fairbridge Inn Express Chesterton
713 Plaza Dr. Chesterton IN
$71 nightly
The price is $80 total per night from Apr 24 to Apr 25
$80 total
Apr 24 - Apr 25
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 (347 reviews)
Air/heat unit didn’t work. Had to return to front desk multiple times as key card would stop working. Night Front desk staff was dismissive and acted agitated when asked questions.
Reviewed on Apr 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.
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.
Need a Car For After Your Flight?
Special
Schiller Park, Illinois, USA
$9
$51 total
found 1 day ago
Midsize
Schiller Park, Illinois, USA
$11
$54 total
found 1 day ago
Standard
Schiller Park, Illinois, USA
$11
$56 total
found 1 day ago
Compact SUV
Schiller Park, Illinois, USA
$14
$63 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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