Cheap Flights to Chesterton from $21

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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 $51 and $21 for one-way flights to Chesterton for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
CMHChicagoMay 28 to May 31$125
CMHChicagoMay 14 to June 1$136
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CMHChicagoMay 4 to May 14$273
CMHChicagoMay 4 to May 14$275
*Prices include taxes and fees

Chesterton Flight Information

Traveling to
Chesterton
Lowest Price
$51
Number of Airlines Serving
Airlines Serving
Spirit Airlines, American 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

Fairbridge Inn Express Chesterton

2 out of 5
713 Plaza Dr., Chesterton, IN
The price is $74 per night from Apr 29 to Apr 30
$74
per night
Apr 29 - Apr 30
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.4/10 (206 reviews)
"Always friendly staff!"

Reviewed on Mar 9, 2024

Fairbridge Inn Express Chesterton
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
The price is $93 per night from May 13 to May 14
$93
per night
May 13 - May 14
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and WiFi. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
8.4/10 Very Good! (967 reviews)
"Hotel was extremely well kept & breakfast was very good. Also beautiful view of the lake"

Reviewed on Apr 22, 2024

Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
The price is $90 per night from Apr 28 to Apr 29
$90
per night
Apr 28 - Apr 29
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
7.8/10 Good! (692 reviews)
"I liked clean quite, and safe, not to mention beautiful scenery of lake."

Reviewed on Apr 18, 2024

Waterbird Lakeside Inn
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

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
The price is $90 per night from Apr 28 to Apr 29
$90
per night
Apr 28 - Apr 29
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
7.8/10 Good! (692 reviews)
"I liked clean quite, and safe, not to mention beautiful scenery of lake."

Reviewed on Apr 18, 2024

Waterbird Lakeside Inn
Quality Inn Chesterton near Indiana Dunes National Park I-94

Quality Inn Chesterton near Indiana Dunes National Park I-94

2.5 out of 5
418 Council Road, Chesterton, IN
The price is $76 per night from May 27 to May 28
$76
per night
May 27 - May 28
Stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular ...
7.8/10 Good! (475 reviews)
"I spent one night here in February 2024. It was a perfect spot for a one night stop mid road trip. The woman who checked me in when I arrived was very friendly. I went downstairs for breakfast 10 minutes before it ended only expecting to get a banana and a cup of coffee, but the woman running the ..."

Reviewed on Feb 25, 2024

Quality Inn Chesterton near Indiana Dunes National Park I-94
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
The price is $93 per night from May 13 to May 14
$93
per night
May 13 - May 14
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and WiFi. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
8.4/10 Very Good! (967 reviews)
"Hotel was extremely well kept & breakfast was very good. Also beautiful view of the lake"

Reviewed on Apr 22, 2024

Best Western Indian Oak
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
Great for families

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
The price is $93 per night from May 13 to May 14
$93
per night
May 13 - May 14
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and WiFi. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
8.4/10 Very Good! (967 reviews)

Families like: Indoor pools, close to beach, extra beds/cribs, free breakfast for the whole family

Travelers say...
"Hotel was extremely well kept & breakfast was very good. Also beautiful view of the lake"

Reviewed on Apr 22, 2024

Best Western Indian Oak
Hilton Garden Inn Chesterton
Great for families

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard, Chesterton, IN
The price is $121 per night from May 27 to May 28
$121
per night
May 27 - May 28
Stay at this 3-star business-friendly hotel in Chesterton. Enjoy free parking, breakfast, and room service. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (968 reviews)

Families like: Indoor pools, extra beds/cribs, laundry

Travelers say...
"Great hotel! Amenities are a plus they have a laundry room with a large washer and dryer for $2. Staff was sweet and professional, she gave my puppies treats! Rooms are nice and bed is comfortable!"

Reviewed on Apr 15, 2024

Hilton Garden Inn Chesterton
Quality Inn Chesterton near Indiana Dunes National Park I-94
Great for families

Quality Inn Chesterton near Indiana Dunes National Park I-94

2.5 out of 5
418 Council Road, Chesterton, IN
The price is $76 per night from May 27 to May 28
$76
per night
May 27 - May 28
Stay at this business-friendly hotel in Chesterton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular ...
7.8/10 Good! (475 reviews)

Families like: Bicycle rentals nearby, extra beds/cribs, free breakfast for the whole family

Travelers say...
"I spent one night here in February 2024. It was a perfect spot for a one night stop mid road trip. The woman who checked me in when I arrived was very friendly. I went downstairs for breakfast 10 minutes before it ended only expecting to get a banana and a cup of coffee, but the woman running the ..."

Reviewed on Feb 25, 2024

Quality Inn Chesterton near Indiana Dunes National Park I-94
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Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

2 out of 5
713 Plaza Dr., Chesterton, IN
The price is $74 per night from Apr 29 to Apr 30
$74
per night
Apr 29 - Apr 30
Stay at this hotel in Chesterton. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.4/10 (206 reviews)
"Always friendly staff!"

Reviewed on Mar 9, 2024

Fairbridge Inn Express Chesterton
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

Prices and availability subject to change. Additional terms may apply.
JW Marriott Chicago
Pendry Chicago
Trump International Hotel & Tower Chicago
Don't see what you're looking for?
See all available trips from CMH-All Airports to Chesterton
View all trips

Chesterton flight + hotel packages - first class flights

Prices and availability subject to change. Additional terms may apply.
Freehand Chicago
Hampton Inn Chicago North-Loyola Station
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
Don't see what you're looking for?
See all available trips from CMH-All Airports to Chesterton
View all trips

Need a Car For After Your Flight?

Frequently asked questions

Which airlines fly to Chesterton?
Packed and ready to roam the world? Hoping to kick off your big adventure in Chesterton? A few of the 20 airlines that fly here are:

  • United Airlines
  • American Airlines
  • Southwest Airlines

What airport is best to fly into Chesterton?
There are two airports in Chesterton. If you touch down at O’Hare Intl. Airport (ORD), you’ll be 50 mi from the center of town. The second option is Chicago Airport, around 40 mi from all the action of the downtown area.
Where to stay in Chesterton
Life is one epic journey, so why not get out there and truly experience it in Chesterton? You can start by selecting from the 63 terrific properties available through Travelocity.The Riley’s Railhouse Bed & Breakfast and the Sweet Home in Chesterton are our suggested accommodations in Chesterton. Make a reservation and then you can get down to the fun stuff — booking your exciting getaway activities.
Places to visit in Chesterton
Witness beautiful scenery and appreciate nature at Indiana Dunes National Park. Need some more options? Imagine you’ve been transported back to the days of your ancestors as you explore Lustron House, a local historic residence. And that’s not all there is. Experience an authentic insight into life on the land at Chellberg Farm. Guests can meet the farmers, pet an animal or two and learn all about how a real farm works.
How to get through airport security fast when traveling to Chesterton
Make your trip to Chesterton a little bit easier by following these clever security tips:

  • Ensure your boarding pass and passport are not difficult to reach. You will be instructed to show them straightaway.
  • Belts, wallets and power banks are to be put in a bin for X-raying. If you walk into the body scanner with any of these items, you’ll be instructed to turn back and remove them.
  • Electronics such as phones, laptops and cameras will need to be sent through the X-ray machine separately. Be sure to have them within easy reach.
  • Toothpaste, lip balm and other toiletry items in gel, liquid or cream form need to be stored in containers no larger than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear zip-lock plastic bag.
  • The airport security may ask you to take off your shoes in preparation for entering the body scanner. Pick a pair that slip off easily. There’s nothing worse than having to do up your laces again and again.
  • Some countries have strict biosecurity laws. Think about where you’re going to and whether or not it’s permissible to fly with unpackaged foods.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.