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Chesterton

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Chesterton Flights as Low as $85

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Fri, Sep 12 - Mon, Sep 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Sep 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Sep 15, priced at $85 found 1 day ago
Frontier Airlines
Sat, Sep 6 - Wed, Sep 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $85 found 1 day ago
Frontier Airlines
Sat, Sep 13 - Sat, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$122 Roundtrip, found 20 hours ago
$122
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, Sep 13 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $122 found 20 hours ago
Spirit Airlines
Sat, Sep 13 - Sat, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$124 Roundtrip, found 20 hours ago
$124
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Sat, Sep 13 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 20, priced at $124 found 20 hours ago
United
Sat, Dec 6 - Sat, Dec 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 5 hours ago
$132
Roundtrip
found 5 hours ago
Select United flight, departing Sat, Dec 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 6, priced at $132 found 5 hours ago
American Airlines
Sat, Oct 18 - Sat, Oct 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 3 hours ago
$134
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Sat, Oct 18 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Oct 18, priced at $134 found 3 hours ago
Frontier Airlines
Fri, Oct 31 - Sat, Nov 1
ONT
Los Angeles - Ontario Intl.
ORD
O'Hare Intl.
$168 Roundtrip, found 13 hours ago
$168
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Los Angeles - Ontario Intl. to O'Hare Intl., returning Sat, Nov 1, priced at $168 found 13 hours ago
Frontier Airlines
Sun, Sep 7 - Thu, Sep 11
ONT
Los Angeles - Ontario Intl.
MDW
Midway Intl.
$173 Roundtrip, found 20 hours ago
$173
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sun, Sep 7 from Los Angeles - Ontario Intl. to Midway Intl., returning Thu, Sep 11, priced at $173 found 20 hours ago
Delta
Sat, Dec 6 - Sat, Dec 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$192 Roundtrip, found 5 hours ago
$192
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Dec 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 6, priced at $192 found 5 hours ago
Frontier Airlines
Sat, Sep 6 - Sun, Sep 7
LAX
Los Angeles Intl.
MDW
Midway Intl.
$201 Roundtrip, found 20 hours ago
$201
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Los Angeles Intl. to Midway Intl., returning Sun, Sep 7, priced at $201 found 20 hours ago
Spirit Airlines
Sat, Sep 6 - Sat, Sep 13
CUN
Cancun Intl.
ORD
O'Hare Intl.
$218 Roundtrip, just found
$218
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Sep 6 from Cancun Intl. to O'Hare Intl., returning Sat, Sep 13, priced at $218 just found
Alaska Airlines
Tue, Oct 21 - Wed, Oct 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$220 Roundtrip, found 12 hours ago
$220
Roundtrip
found 12 hours ago
Select Alaska Airlines flight, departing Tue, Oct 21 from Los Angeles Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $220 found 12 hours ago
Sun Country Airlines
Fri, Oct 31 - Mon, Nov 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$290 Roundtrip, found 12 hours ago
$290
Roundtrip
found 12 hours ago
Select Sun Country Airlines flight, departing Fri, Oct 31 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 3, priced at $290 found 12 hours ago
JetBlue Airways
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$299 Roundtrip, found 6 hours ago
$299
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Wed, Oct 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $299 found 6 hours ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Dec 23 - Tue, Dec 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$325 Roundtrip, found 5 hours ago
$325
Roundtrip
found 5 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Dec 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 30, priced at $325 found 5 hours ago
Volaris
Tue, Aug 26 - Thu, Aug 28
CUN
Cancun Intl.
ORD
O'Hare Intl.
$859 Roundtrip, found 21 hours ago
$859
Roundtrip
found 21 hours ago
Select Volaris flight, departing Tue, Aug 26 from Cancun Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $859 found 21 hours ago

Cheap Flights to Chesterton

Fall in love at first flight with your vacation to Chesterton by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chesterton on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chesterton, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chesterton

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chesterton with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the RFD airport.

What is the cheapest month to fly to Chesterton?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chesterton are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chesterton?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chesterton.

What airport is best to fly into Chesterton?

When you’re planning your trip to Chesterton, convenience is the name of the game. Luckily, Chesterton Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Chesterton must-do list.

How much are flights to Chesterton?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chesterton on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $85, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chesterton?

The trick to saving a stack of cash on your flight to Chesterton? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $85 right now, why wait?

Chesterton Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$84

Last Minute Hotel Deals in Chesterton

Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
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 ...
8.8/10 Excellent! (1,003 reviews)
"Charm"

Reviewed on Aug 22, 2025

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Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Stay at this hotel in Chesterton. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (1,000 reviews)
"Very lovely place to stay. The lake is very pretty with lots of wildlife. Although the hotel is older, it is very quaint. It is also very quiet, the staff were very pleasant and helpful, and the room and bathroom were so very nice. I’d definitely stay here again."

Reviewed on Aug 18, 2025

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Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
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! (910 reviews)
Good stopping place.
"We checked in and found the room to be nice for the cost. The only downside is that it is above a lake and the humidity in Indiana at this time of year is high so the room was humid. The A/C worked fine and cooled the room, but the level of humidity was higher then I preferred. There was no musty ..."

Reviewed on Aug 22, 2025

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Waterbird Lakeside Inn
Comfort Inn & Suites Porter near Indiana Dunes

Comfort Inn & Suites Porter near Indiana Dunes

2.5 out of 5
1800 West US Highway 20, Chesterton, IN
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! (1,001 reviews)
"Our bathroom shower and area around it was in bad shape , the shower curtain rod was not attached properly so it was allowing water to leak outside of area and it has been that way for a long time because the damp odor was very prominent!!"

Reviewed on Aug 20, 2025

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Comfort Inn & Suites Porter near Indiana Dunes
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
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! (669 reviews)
"Good stay in general"

Reviewed on Aug 22, 2025

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

Hilton Garden Inn Chesterton

3 out of 5
501 Gateway Boulevard, Chesterton, IN
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! (1,000 reviews)
"Beds were so comfortable."

Reviewed on Aug 19, 2025

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Hilton Garden Inn Chesterton
Fairbridge Inn Express Chesterton

Fairbridge Inn Express Chesterton

2 out of 5
713 Plaza Dr., Chesterton, IN
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 (326 reviews)
"Beds were a little hard .Staff was friendly and vary helful .Overall a nice place to stay."

Reviewed on Aug 18, 2025

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Fairbridge Inn Express Chesterton
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
Stay at this 4-star beach hotel in East Chicago. Enjoy 5 restaurants, a marina, and a casino. Our guests praise the helpful staff and the clean rooms in our ...
8.4/10 Very Good! (1,006 reviews)
"I've always loved the Ameristar Casino hotel rooms. They offer smoking/they have an iron and board in room/fridge in room {although I understand why the microwaves were removed long ago}/the bathroom especially. Separate toilet room full bathtub and separate shower! It's the cost that's hinder my ..."

Reviewed on Aug 23, 2025

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Ameristar Casino Hotel East Chicago
See all 1,376 properties in 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.