Cheap Flights to Chesterton from $32
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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 $114 and $32 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.
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | March 10 to March 11 | $130 |
| LAX | Chicago | February 11 to February 24 | $148 |
| LAX | Rockford | January 17 to January 20 | $159 |
| FCO | Chicago | January 14 to January 25 | $574 |
| HKG | Chicago | February 2 to March 2 | $846 |
| HKG | Chicago | January 21 to March 4 | $947 |
| PEK | Chicago | March 9 to March 17 | $950 |
| CAN | Chicago | February 26 to March 16 | $950 |
| PVG | Chicago | January 20 to April 30 | $993 |
| SZX | Chicago | January 5 to January 18 | $2,097 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | December 28 to January 14 | $350 |
| LAX | Chicago | December 27 to January 1 | $414 |
| LAX | Rockford | December 27 to January 1 | $614 |
| FCO | Chicago | December 27 to December 31 | $823 |
| HKG | Chicago | December 28 to January 2 | $1,105 |
| PVG | Chicago | December 28 to April 15 | $1,214 |
| XIY | Chicago | December 28 to January 1 | $1,232 |
Chesterton Flight Information
Traveling to | Chesterton |
|---|---|
Lowest Price | $114 |
Number of Airlines Serving | |
Airlines Serving | Spirit Airlines, Sun Country 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 Dec 26 to Dec 27
$90 total
Dec 26 - Dec 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 (343 reviews)
Staff was amazing. Debbie was super friendly and helpful when I locked myself out.
Reviewed on Nov 2, 2025
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$93 nightly
The price is $105 total per night from Dec 31 to Jan 1
$105 total
Dec 31 - Jan 1, 2026
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! (1,002 reviews)
Hotel is in a great location, safe, and many dining options close by. Was a little sad the lake was frozen and didn't get to see the usual birds. Breakfast was the same both mornings, was hoping for a little variety. I guess staying if December is a bit different.
Reviewed on Dec 21, 2025
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
$90 nightly
The price is $101 total per night from Dec 26 to Dec 27
$101 total
Dec 26 - Dec 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! (989 reviews)
We had a plumbing problem and it was immediately fixed. We were swapped rooms so that it wouldnt interfere with our plans. Comfortable beds and a beautiful view of the lake.
Reviewed on Dec 14, 2025
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
$90 nightly
The price is $101 total per night from Dec 26 to Dec 27
$101 total
Dec 26 - Dec 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! (989 reviews)
We had a plumbing problem and it was immediately fixed. We were swapped rooms so that it wouldnt interfere with our plans. Comfortable beds and a beautiful view of the lake.
Reviewed on Dec 14, 2025
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$77 nightly
The price is $87 total per night from Jan 14 to Jan 15
$87 total
Jan 14 - Jan 15, 2026
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! (719 reviews)
Good stay
Reviewed on Dec 21, 2025
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
$93 nightly
The price is $105 total per night from Dec 31 to Jan 1
$105 total
Dec 31 - Jan 1, 2026
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! (1,002 reviews)
Hotel is in a great location, safe, and many dining options close by. Was a little sad the lake was frozen and didn't get to see the usual birds. Breakfast was the same both mornings, was hoping for a little variety. I guess staying if December is a bit different.
Reviewed on Dec 21, 2025
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 Dec 31 to Jan 1
$105 total
Dec 31 - Jan 1, 2026
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! (1,002 reviews)
Hotel is in a great location, safe, and many dining options close by. Was a little sad the lake was frozen and didn't get to see the usual birds. Breakfast was the same both mornings, was hoping for a little variety. I guess staying if December is a bit different.
Reviewed on Dec 21, 2025
Hilton Garden Inn Chesterton
501 Gateway Boulevard Chesterton IN
$112 nightly
The price is $125 total per night from Jan 11 to Jan 12
$125 total
Jan 11 - Jan 12, 2026
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! (1,001 reviews)
Very clean room Staff friendly
Reviewed on Dec 7, 2025
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road Chesterton IN
$77 nightly
The price is $87 total per night from Jan 14 to Jan 15
$87 total
Jan 14 - Jan 15, 2026
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! (719 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 Dec 26 to Dec 27
$90 total
Dec 26 - Dec 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 (343 reviews)
Staff was amazing. Debbie was super friendly and helpful when I locked myself out.
Reviewed on Nov 2, 2025
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
$7
$46 total
found 7 hours ago
Midsize SUV
Schiller Park, Illinois, USA
$10
$52 total
found 7 hours ago
Compact SUV
Schiller Park, Illinois, USA
$11
$55 total
found 7 hours ago
Standard
Schiller Park, Illinois, USA
$13
$59 total
found 7 hours ago
Lowest prices found within the past 7 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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