Cheap Flights to Chesterton from $30
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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 $63 and $30 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.
ORD
O'Hare Intl.
$63 Roundtrip, found 2 hours ago
$63
Roundtrip
found 2 hours ago
LGA
LaGuardia
ORD
O'Hare Intl.
$63 Roundtrip, found 8 hours ago
$63
Roundtrip
found 8 hours ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | December 5 to December 13 | $83 |
| LAX | Chicago | January 8 to January 12 | $142 |
| LAX | Rockford | December 10 to December 14 | $161 |
| FCO | Chicago | January 16 to January 25 | $564 |
| CAN | Chicago | December 26 to April 24 | $714 |
| HKG | Chicago | January 29 to February 19 | $786 |
| FCO | Chicago | December 23 to January 6 | $893 |
| PEK | Chicago | November 22 to December 5 | $916 |
| PVG | Chicago | December 15 to December 31 | $997 |
| FOC | Chicago | December 25 to December 29 | $1,005 |
| CTU | Chicago | November 20 to November 24 | $1,020 |
| SZX | Chicago | November 17 to November 24 | $1,162 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | November 15 to November 18 | $171 |
| LAX | Chicago | November 16 to November 20 | $342 |
| FCO | Chicago | November 14 to November 27 | $648 |
| LAX | Rockford | November 14 to November 16 | $757 |
| HKG | Chicago | November 14 to November 17 | $877 |
| PEK | Chicago | November 15 to December 8 | $919 |
| PVG | Chicago | November 16 to December 1 | $1,118 |
Chesterton Flight Information
Traveling to | Chesterton |
|---|---|
Lowest Price | $63 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Spirit 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
$89 nightly
The price is $100 total per night from Nov 11 to Nov 12
$100 total
Nov 11 - Nov 12
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 (339 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 Nov 17 to Nov 18
$105 total
Nov 17 - Nov 18
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 pool and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,001 reviews)
Though the buildings decor may be a little dated it was one of the cleanest hotels I've stayed at all appliances were in the room and working normally they say refrigerator in room and don't have 1 but indian oak delivered on theirs!! Close to the interstate and places to shop also 2 minutes from ...
Reviewed on Nov 8, 2025
Waterbird Lakeside Inn
556 Indian Boundary Road, Chesterton, IN
$90 nightly
The price is $101 total per night from Nov 11 to Nov 12
$101 total
Nov 11 - Nov 12
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! (977 reviews)
The room was so clean and spacious. The view was spectacular! The color of the fall leaves, the refraction of the sun off the lake. Morning dew rolling across the lake. Extremely quiet,in November. A Zen two day retreat. Highly recommended! Mental vacations are a necessity.
Reviewed on Nov 9, 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 Nov 11 to Nov 12
$101 total
Nov 11 - Nov 12
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! (977 reviews)
The room was so clean and spacious. The view was spectacular! The color of the fall leaves, the refraction of the sun off the lake. Morning dew rolling across the lake. Extremely quiet,in November. A Zen two day retreat. Highly recommended! Mental vacations are a necessity.
Reviewed on Nov 9, 2025
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road, Chesterton, IN
$78 nightly
The price is $88 total per night from Dec 11 to Dec 12
$88 total
Dec 11 - Dec 12
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! (707 reviews)
Five stars for the great staff! I wish there handnt been mold in the tub grout. One minor annoyance that I didn’t bring up since I was there for a short time is that when the fan isn’t set to continuous, it squeals when it shuts off and sounds like someone coming in a door. Just FYI—I think the water ...
Reviewed on Oct 30, 2025
Best Western Indian Oak
558 Indian Boundary Road, Chesterton, IN
$93 nightly
The price is $105 total per night from Nov 17 to Nov 18
$105 total
Nov 17 - Nov 18
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 pool and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,001 reviews)
Though the buildings decor may be a little dated it was one of the cleanest hotels I've stayed at all appliances were in the room and working normally they say refrigerator in room and don't have 1 but indian oak delivered on theirs!! Close to the interstate and places to shop also 2 minutes from ...
Reviewed on Nov 8, 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 Nov 17 to Nov 18
$105 total
Nov 17 - Nov 18
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 pool and the helpful staff in our reviews. ...
8.4/10 Very Good! (1,001 reviews)
Though the buildings decor may be a little dated it was one of the cleanest hotels I've stayed at all appliances were in the room and working normally they say refrigerator in room and don't have 1 but indian oak delivered on theirs!! Close to the interstate and places to shop also 2 minutes from ...
Reviewed on Nov 8, 2025
Hilton Garden Inn Chesterton
501 Gateway Boulevard, Chesterton, IN
$114 nightly
The price is $128 total per night from Nov 23 to Nov 24
$128 total
Nov 23 - Nov 24
Total with taxes and fees
Stay at this 3-star 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! (1,011 reviews)
👍
Reviewed on Oct 31, 2025
Quality Inn Chesterton near Indiana Dunes National Park I-94
418 Council Road, Chesterton, IN
$78 nightly
The price is $88 total per night from Dec 11 to Dec 12
$88 total
Dec 11 - Dec 12
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! (707 reviews)
Five stars for the great staff! I wish there handnt been mold in the tub grout. One minor annoyance that I didn’t bring up since I was there for a short time is that when the fan isn’t set to continuous, it squeals when it shuts off and sounds like someone coming in a door. Just FYI—I think the water ...
Reviewed on Oct 30, 2025
Save an average of 15% on thousands of hotels when you're signed in
Fairbridge Inn Express Chesterton
713 Plaza Dr., Chesterton, IN
$89 nightly
The price is $100 total per night from Nov 11 to Nov 12
$100 total
Nov 11 - Nov 12
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 (339 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.
Need a Car For After Your Flight?
Special
Schiller Park, Illinois, USA
$4
$38 total
found 3 days ago
Midsize SUV
Schiller Park, Illinois, USA
$7
$45 total
found 3 days ago
Compact SUV
Schiller Park, Illinois, USA
$8
$46 total
found 3 days ago
Standard
Schiller Park, Illinois, USA
$9
$49 total
found 3 days ago
Lowest prices found within the past 3 days. 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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