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Cheap flights from Stillwater to Chicago from $423

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 10/14. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Stillwater to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
3:09 pm - 10:10 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
7h 01m1 stop Dallas/Fort Worth
American Airlines Logo
8:14 am - 2:39 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
6h 25m1 stop Dallas/Fort Worth
$423American Airlines
Wed, Oct 14 - Sat, Oct 17
American Airlines Logo
3:39 pm - 11:30 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
7h 51m1 stop Dallas/Fort Worth
American Airlines Logo
4:57 pm - 10:46 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
5h 49m1 stop Dallas/Fort Worth
$485American Airlines
Tue, Sep 1 - Sat, Sep 5
American Airlines Logo
6:05 am - 12:15 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
6h 10m1 stop Dallas/Fort Worth
American Airlines Logo
3:54 pm - 10:46 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
6h 52m1 stop Dallas/Fort Worth
$487American Airlines
Mon, Aug 31 - Fri, Sep 4
American Airlines Logo
2:55 pm - 10:00 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
7h 05m1 stop Dallas/Fort Worth
American Airlines Logo
8:05 am - 2:24 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
6h 19m1 stop Dallas/Fort Worth
$641American Airlines
Tue, Dec 22 - Sat, Dec 26
American Airlines Logo
6:00 am - 3:32 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
9h 32m2 stops Dallas/Fort Worth Springfield-Branson
American Airlines Logo
12:02 pm - 10:53 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
10h 51m1 stop Dallas/Fort Worth
$791American Airlines
Thu, Nov 26 - Sat, Dec 5
American Airlines Logo
6:05 am - 2:20 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
8h 15m2 stops Dallas/Fort Worth Charlotte Douglas
American Airlines Logo
3:50 pm - 10:46 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
6h 56m1 stop Dallas/Fort Worth
$881American Airlines
Wed, Oct 14 - Sat, Oct 17
American Airlines Logo
6:05 am - 2:22 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
8h 17m2 stops Dallas/Fort Worth Charlotte Douglas
American Airlines Logo
9:40 am - 3:34 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
5h 54m1 stop Dallas/Fort Worth
$908American Airlines
Tue, Sep 1 - Sat, Sep 5
American Airlines Logo
6:05 am - 3:00 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
8h 55m2 stops Dallas/Fort Worth Oklahoma City Will Rogers World
American Airlines Logo
3:00 pm - 10:44 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
7h 44m1 stop Dallas/Fort Worth
$963American Airlines
Thu, Sep 24 - Fri, Sep 25
American Airlines Logo
6:05 am - 2:19 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
8h 14m2 stops Dallas/Fort Worth Columbia Regional
American Airlines Logo
8:20 am - 3:09 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
6h 49m1 stop Dallas/Fort Worth
$980American Airlines
Mon, Aug 31 - Fri, Sep 4
American Airlines Logo
2:55 pm - 9:50 pmSWO  Stillwater Searcy Fld-ORD Chicago O'Hare Intl
6h 55m2 stops Dallas/Fort Worth Tulsa
American Airlines Logo
3:27 pm - 10:44 pmORD  Chicago O'Hare Intl-SWO Stillwater Searcy Fld
7h 17m2 stops Little Rock Dallas/Fort Worth
$1,274American Airlines
Tue, Dec 22 - Sat, Dec 26

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American Airlines flights from Stillwater to Chicago

Our best American Airlines deals on Stillwater to Chicago flight tickets
American Airlines
Oct 14
SWO3:09 pmStillwater Searcy Fld
7h 01m
1 stop
ORD10:10 pmChicago O'Hare Intl
Oct 17
ORD8:14 amChicago O'Hare Intl
6h 25m
1 stop
SWO2:39 pmStillwater Searcy Fld
$423
American Airlines
Sep 1
SWO3:39 pmStillwater Searcy Fld
7h 51m
1 stop
ORD11:30 pmChicago O'Hare Intl
Sep 5
ORD4:57 pmChicago O'Hare Intl
5h 49m
1 stop
SWO10:46 pmStillwater Searcy Fld
$485
American Airlines
Aug 31
SWO6:05 amStillwater Searcy Fld
6h 10m
1 stop
ORD12:15 pmChicago O'Hare Intl
Sep 4
ORD3:54 pmChicago O'Hare Intl
6h 52m
1 stop
SWO10:46 pmStillwater Searcy Fld
$487

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 August 18, 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

Cheapest round-trip

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Wed 10/14

3:09 pm-10:10 pm

1 stop7h 01m

Chicago O'Hare Intl

Sat 10/17

8:14 am-2:39 pm

1 stop6h 25m

$423

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Tue 9/1

3:39 pm-11:30 pm

1 stop7h 51m

Chicago O'Hare Intl

Sat 9/5

4:57 pm-10:46 pm

1 stop5h 49m

$485
Quickest round-trip

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Mon 8/31

6:05 am-12:15 pm

1 stop6h 10m

Chicago O'Hare Intl

Fri 9/4

3:54 pm-10:46 pm

1 stop6h 52m

$487

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Tue 12/22

2:55 pm-10:00 pm

1 stop7h 05m

Chicago O'Hare Intl

Sat 12/26

8:05 am-2:24 pm

1 stop6h 19m

$641

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Thu 11/26

6:00 am-3:32 pm

2 stops9h 32m

Chicago O'Hare Intl

Sat 12/5

12:02 pm-10:53 pm

1 stop10h 51m

$791

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Wed 10/14

6:05 am-2:20 pm

2 stops8h 15m

Chicago O'Hare Intl

Sat 10/17

3:50 pm-10:46 pm

1 stop6h 56m

$881

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Tue 9/1

6:05 am-2:22 pm

2 stops8h 17m

Chicago O'Hare Intl

Sat 9/5

9:40 am-3:34 pm

1 stop5h 54m

$908

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Thu 9/24

6:05 am-3:00 pm

2 stops8h 55m

Chicago O'Hare Intl

Fri 9/25

3:00 pm-10:44 pm

1 stop7h 44m

$963

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Mon 8/31

6:05 am-2:19 pm

2 stops8h 14m

Chicago O'Hare Intl

Fri 9/4

8:20 am-3:09 pm

1 stop6h 49m

$980

StillwaterChicago

SWO Stillwater Searcy Fld - ORD Chicago O'Hare Intl

SWOORD

Stillwater Searcy Fld

Tue 12/22

2:55 pm-9:50 pm

2 stops6h 55m

Chicago O'Hare Intl

Sat 12/26

3:27 pm-10:44 pm

2 stops7h 17m

$1,274

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Chicago from

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 44% 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

Best Price Found

$423

Fastest flight time

6h 10m

Direct flights

None
The best flight deal from Stillwater to Chicago found on momondo in the last 72 hours is $423
The fastest flight from Stillwater to Chicago takes 6h 10m
There are no direct flights from Stillwater to Chicago. There are no popular flight routes from Stillwater to Chicago.
Search flight deals

Frequently asked questions about flying from Stillwater to Chicago

  • 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 10m.

  • 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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