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Cheap flights from Stillwater to Chicago from $457

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Stillwater to Chicago departing on 2/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
2:25 pm - 8:40 pm
SWO
-
ORD
6h 15m
1 stop
American Airlines Logo
8:26 am - 1:36 pm
ORD
-
SWO
5h 10m
1 stop
$457American Airlines
Wed, Feb 25 - Sun, Mar 1
American Airlines Logo
2:35 pm - 10:00 pm
SWO
-
ORD
7h 25m
1 stop
American Airlines Logo
2:39 pm - 10:59 pm
ORD
-
SWO
8h 20m
2 stops
$785American Airlines
Sat, Feb 28 - Wed, Mar 4
American Airlines Logo
6:00 am - 2:00 pm
SWO
-
ORD
8h 00m
2 stops
American Airlines Logo
8:26 am - 1:36 pm
ORD
-
SWO
5h 10m
1 stop
$812American Airlines
Wed, Feb 25 - Sun, Mar 1
American Airlines Logo
6:00 am - 1:04 pm
SWO
-
ORD
7h 04m
1 stop
American Airlines Logo
2:01 pm - 10:59 pm
ORD
-
SWO
8h 58m
2 stops
$848American Airlines
Thu, Feb 26 - Mon, Mar 2

American Airlines flights from Stillwater to Chicago

Our best American Airlines deals on Stillwater to Chicago flight tickets
American Airlines
Feb 25
SWO2:25 pmStillwater Searcy Fld
6h 15m
1 stop
ORD8:40 pmChicago O'Hare Intl
Mar 1
ORD8:26 amChicago O'Hare Intl
5h 10m
1 stop
SWO1:36 pmStillwater Searcy Fld
$457
American Airlines
Feb 14
SWO6:00 amStillwater Searcy Fld
5h 03m
1 stop
ORD11:03 amChicago O'Hare Intl
Feb 16
ORD8:26 amChicago O'Hare Intl
5h 10m
1 stop
SWO1:36 pmStillwater Searcy Fld
$581
American Airlines
Feb 28
SWO2:35 pmStillwater Searcy Fld
7h 25m
1 stop
ORD10:00 pmChicago O'Hare Intl
Mar 4
ORD2:39 pmChicago O'Hare Intl
8h 20m
2 stops
SWO10:59 pmStillwater Searcy Fld
$785

momondo Fare Finder

 
Customize your flight search to find flights from Stillwater to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 13, 2026.
Use the filters below to find and compare flights from Stillwater to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Wed 2/25

2:25 pm-8:40 pm

1 stop6h 15m

Chicago O'Hare Intl

Sun 3/1

8:26 am-1:36 pm

1 stop5h 10m

$457

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Sat 2/28

2:35 pm-10:00 pm

1 stop7h 25m

Chicago O'Hare Intl

Wed 3/4

2:39 pm-10:59 pm

2 stops8h 20m

$785

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Wed 2/25

6:00 am-2:00 pm

2 stops8h 00m

Chicago O'Hare Intl

Sun 3/1

8:26 am-1:36 pm

1 stop5h 10m

$812

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Thu 2/26

6:00 am-1:04 pm

1 stop7h 04m

Chicago O'Hare Intl

Mon 3/2

2:01 pm-10:59 pm

2 stops8h 58m

$848

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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How to get the cheapest flight ticket from Stillwater to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What airlines fly to Chicago?

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Stillwater according to our data. American Airlines is the first choice among our users, with 55% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 4 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

When to book flights from Stillwater to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Stillwater to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Stillwater to Chicago (SWO to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Stillwater to Chicago

Fastest flight time

6h 15m

Direct flights

None
The fastest flight from Stillwater to Chicago takes 6h 15m
There are no direct flights from Stillwater to Chicago. There are no popular flight routes from Stillwater to Chicago.
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  • How far is Stillwater Searcy Fld to Chicago by plane?

    Chicago is 643.0 mi away from Stillwater Searcy Fld. A reasonable flight in good conditions will take 6h 15m.

  • When did momondo last update prices for flights from Stillwater Searcy Fld Airport to Chicago?

    Prices for flights from Stillwater Searcy Fld Airport to Chicago were last updated today.

  • How old do you have to be to fly from Stillwater Searcy Fld Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Stillwater Searcy Fld Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Stillwater to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Stillwater to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Stillwater to Chicago with flexible booking policies on momondo?

All flight searches from Stillwater to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Stillwater to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Stillwater.

I’m not ready to book a flight from Stillwater to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Stillwater to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport