Cheap flights from Stillwater to Chicago from $187

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Stillwater to Chicago departing on 10/24. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.

Find the cheapest flights from Stillwater to Chicago (SWO-CHI)

Cheap round-trip flights

American Airlines Logo
2:30 pm - 8:02 pmSWO-ORD
5h 32m1 stop
American Airlines Logo
3:58 pm - 10:35 pmORD-SWO
6h 37m1 stop
$373American Airlines
Find Deal
Thu, Sep 25 - Thu, Oct 2
American Airlines Logo
6:00 am - 12:36 pmSWO-ORD
6h 36m1 stop
American Airlines Logo
6:45 am - 2:02 pmORD-SWO
7h 17m1 stop
$538American Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
American Airlines Logo
2:30 pm - 8:02 pmSWO-ORD
5h 32m1 stop
American Airlines Logo
5:16 pm - 10:37 pmORD-SWO
5h 21m1 stop
$576American Airlines
Find Deal
Thu, Sep 11 - Mon, Sep 15
American Airlines Logo
6:00 am - 11:00 amSWO-ORD
5h 00m1 stop
American Airlines Logo
8:25 am - 2:00 pmORD-SWO
5h 35m1 stop
$605American Airlines
Find Deal
Wed, Sep 10 - Sun, Sep 14
American Airlines Logo
2:30 pm - 9:05 pmSWO-ORD
6h 35m2 stops
American Airlines Logo
3:58 pm - 10:35 pmORD-SWO
6h 37m1 stop
$710American Airlines
Find Deal
Thu, Sep 25 - Thu, Oct 2
American Airlines Logo
2:30 pm - 9:05 pmSWO-ORD
6h 35m2 stops
American Airlines Logo
5:16 pm - 10:37 pmORD-SWO
5h 21m1 stop
$732American Airlines
Find Deal
Thu, Sep 11 - Mon, Sep 15
American Airlines Logo
6:00 am - 11:00 amSWO-ORD
5h 00m1 stop
American Airlines Logo
3:20 pm - 10:35 pmORD-SWO
7h 15m2 stops
$795American Airlines
Find Deal
Wed, Sep 10 - Sun, Sep 14
American Airlines Logo
6:00 am - 10:59 amSWO-ORD
4h 59m1 stop
American Airlines Logo
7:10 am - 2:02 pmORD-SWO
6h 52m2 stops
$848American Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
American Airlines Logo
6:00 am - 3:03 pmSWO-ORD
9h 03m2 stops
American Airlines Logo
3:20 pm - 10:35 pmORD-SWO
7h 15m2 stops
$942American Airlines
Find Deal
Wed, Sep 10 - Sun, Sep 14
American Airlines Logo
2:30 pm - 9:05 pmSWO-ORD
6h 35m2 stops
American Airlines Logo
3:20 pm - 10:37 pmORD-SWO
7h 17m2 stops
$977American Airlines
Find Deal
Thu, Sep 11 - Mon, Sep 15

American Airlines flights from Stillwater to Chicago

Our best American Airlines deals on Stillwater to Chicago flight tickets
American Airlines
Sep 25
SWO2:30 pmStillwater Searcy Fld
5h 32m
1 stop
ORD8:02 pmChicago O'Hare Intl
Oct 2
ORD3:58 pmChicago O'Hare Intl
6h 37m
1 stop
SWO10:35 pmStillwater Searcy Fld
American Airlines
Sep 5
SWO2:30 pmStillwater Searcy Fld
5h 31m
1 stop
ORD8:01 pmChicago O'Hare Intl
Sep 7
ORD8:25 amChicago O'Hare Intl
5h 35m
1 stop
SWO2:00 pmStillwater Searcy Fld
American Airlines
Oct 9
SWO6:00 amStillwater Searcy Fld
6h 36m
1 stop
ORD12:36 pmChicago O'Hare Intl
Oct 13
ORD6:45 amChicago O'Hare Intl
7h 17m
1 stop
SWO2:02 pmStillwater Searcy Fld

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 28, 2025.
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

Thu 9/25

2:30 pm-8:02 pm

1 stop5h 32m

Chicago O'Hare Intl

Thu 10/2

3:58 pm-10:35 pm

1 stop6h 37m

$373

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Thu 10/9

6:00 am-12:36 pm

1 stop6h 36m

Chicago O'Hare Intl

Mon 10/13

6:45 am-2:02 pm

1 stop7h 17m

$538

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Thu 9/11

2:30 pm-8:02 pm

1 stop5h 32m

Chicago O'Hare Intl

Mon 9/15

5:16 pm-10:37 pm

1 stop5h 21m

$576

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Wed 9/10

6:00 am-11:00 am

1 stop5h 00m

Chicago O'Hare Intl

Sun 9/14

8:25 am-2:00 pm

1 stop5h 35m

$605

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Thu 9/25

2:30 pm-9:05 pm

2 stops6h 35m

Chicago O'Hare Intl

Thu 10/2

3:58 pm-10:35 pm

1 stop6h 37m

$710

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Thu 9/11

2:30 pm-9:05 pm

2 stops6h 35m

Chicago O'Hare Intl

Mon 9/15

5:16 pm-10:37 pm

1 stop5h 21m

$732

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Wed 9/10

6:00 am-11:00 am

1 stop5h 00m

Chicago O'Hare Intl

Sun 9/14

3:20 pm-10:35 pm

2 stops7h 15m

$795

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Thu 10/9

6:00 am-10:59 am

1 stop4h 59m

Chicago O'Hare Intl

Mon 10/13

7:10 am-2:02 pm

2 stops6h 52m

$848

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Wed 9/10

6:00 am-3:03 pm

2 stops9h 03m

Chicago O'Hare Intl

Sun 9/14

3:20 pm-10:35 pm

2 stops7h 15m

$942

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Thu 9/11

2:30 pm-9:05 pm

2 stops6h 35m

Chicago O'Hare Intl

Mon 9/15

3:20 pm-10:37 pm

2 stops7h 17m

$977

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

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 is the cheapest airline that flies from Stillwater Searcy Fld to Chicago?

American Airlines is the most popular carrier operating from Stillwater Searcy Fld to Chicago

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 58% 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

Direct flights

None
There are no direct flights from Stillwater to Chicago. There are no popular flight routes 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 4h 59m.

  • 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 9/2
Tue 9/9

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