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Cheap flights from Stillwater to Chicago from $376

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 6/7. 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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Find the cheapest flights from Stillwater to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
3:52 pm - 11:12 pm
SWO
-
ORD
7h 20m
1 stop
American Airlines Logo
8:20 am - 2:54 pm
ORD
-
SWO
6h 34m
1 stop
$413American Airlines
Wed, Oct 14 - Sat, Oct 17
American Airlines Logo
3:06 pm - 9:45 pm
SWO
-
ORD
6h 39m
1 stop
American Airlines Logo
8:20 am - 2:36 pm
ORD
-
SWO
6h 16m
1 stop
$477American Airlines
Sat, May 16 - Wed, May 20
American Airlines Logo
6:05 am - 11:59 am
SWO
-
ORD
5h 54m
1 stop
American Airlines Logo
4:45 pm - 10:48 pm
ORD
-
SWO
6h 03m
1 stop
$571American Airlines
Sat, Jun 6 - Mon, Jun 8
American Airlines Logo
3:35 pm - 9:15 pm
SWO
-
ORD
5h 40m
1 stop
American Airlines Logo
8:19 am - 3:05 pm
ORD
-
SWO
6h 46m
1 stop
$582American Airlines
Mon, Jun 1 - Sun, Jun 7
American Airlines Logo
6:05 am - 11:09 am
SWO
-
ORD
5h 04m
1 stop
American Airlines Logo
9:40 am - 3:05 pm
ORD
-
SWO
5h 25m
1 stop
$585American Airlines
Fri, May 29 - Thu, Jun 4
American Airlines Logo
3:35 pm - 9:15 pm
SWO
-
ORD
5h 40m
1 stop
American Airlines Logo
9:40 am - 3:05 pm
ORD
-
SWO
5h 25m
1 stop
$695American Airlines
Mon, Jun 1 - Sun, Jun 7
American Airlines Logo
6:05 am - 4:19 pm
SWO
-
ORD
10h 14m
2 stops
American Airlines Logo
11:43 am - 10:48 pm
ORD
-
SWO
11h 05m
1 stop
$709American Airlines
Sat, Jun 6 - Mon, Jun 8
American Airlines Logo
3:52 pm - 11:12 pm
SWO
-
ORD
7h 20m
1 stop
American Airlines Logo
6:45 am - 2:54 pm
ORD
-
SWO
8h 09m
2 stops
$796American Airlines
Wed, Oct 14 - Sat, Oct 17
American Airlines Logo
6:05 am - 2:20 pm
SWO
-
ORD
8h 15m
2 stops
American Airlines Logo
4:53 pm - 10:48 pm
ORD
-
SWO
5h 55m
1 stop
$834American Airlines
Wed, Oct 14 - Sat, Oct 17
American Airlines Logo
6:05 am - 2:20 pm
SWO
-
ORD
8h 15m
2 stops
American Airlines Logo
4:53 pm - 10:48 pm
ORD
-
SWO
5h 55m
1 stop
$859American Airlines
Wed, Oct 14 - Sat, Oct 17

American Airlines flights from Stillwater to Chicago O'Hare Intl Airport

Our best American Airlines deals on Stillwater to Chicago O'Hare Intl Airport flight tickets
American Airlines
Oct 14
SWO3:52 pmStillwater Searcy Fld
7h 20m
1 stop
ORD11:12 pmChicago O'Hare Intl
Oct 17
ORD8:20 amChicago O'Hare Intl
6h 34m
1 stop
SWO2:54 pmStillwater Searcy Fld
$413
American Airlines
May 16
SWO3:06 pmStillwater Searcy Fld
6h 39m
1 stop
ORD9:45 pmChicago O'Hare Intl
May 20
ORD8:20 amChicago O'Hare Intl
6h 16m
1 stop
SWO2:36 pmStillwater Searcy Fld
$477
American Airlines
Jun 6
SWO6:05 amStillwater Searcy Fld
5h 54m
1 stop
ORD11:59 amChicago O'Hare Intl
Jun 8
ORD4:45 pmChicago O'Hare Intl
6h 03m
1 stop
SWO10:48 pmStillwater Searcy Fld
$571

momondo Fare Finder

 
Customize your flight search to find flights from Stillwater to Chicago O'Hare Intl Airport 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 May 5, 2026.
Use the filters below to find and compare flights from Stillwater to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Wed 10/14

3:52 pm-11:12 pm

1 stop7h 20m

Chicago O'Hare Intl

Sat 10/17

8:20 am-2:54 pm

1 stop6h 34m

$413

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Sat 5/16

3:06 pm-9:45 pm

1 stop6h 39m

Chicago O'Hare Intl

Wed 5/20

8:20 am-2:36 pm

1 stop6h 16m

$477

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Sat 6/6

6:05 am-11:59 am

1 stop5h 54m

Chicago O'Hare Intl

Mon 6/8

4:45 pm-10:48 pm

1 stop6h 03m

$571

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Mon 6/1

3:35 pm-9:15 pm

1 stop5h 40m

Chicago O'Hare Intl

Sun 6/7

8:19 am-3:05 pm

1 stop6h 46m

$582
Quickest round-trip

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Fri 5/29

6:05 am-11:09 am

1 stop5h 04m

Chicago O'Hare Intl

Thu 6/4

9:40 am-3:05 pm

1 stop5h 25m

$585

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Mon 6/1

3:35 pm-9:15 pm

1 stop5h 40m

Chicago O'Hare Intl

Sun 6/7

9:40 am-3:05 pm

1 stop5h 25m

$695

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Sat 6/6

6:05 am-4:19 pm

2 stops10h 14m

Chicago O'Hare Intl

Mon 6/8

11:43 am-10:48 pm

1 stop11h 05m

$709

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Wed 10/14

3:52 pm-11:12 pm

1 stop7h 20m

Chicago O'Hare Intl

Sat 10/17

6:45 am-2:54 pm

2 stops8h 09m

$796

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Wed 10/14

6:05 am-2:20 pm

2 stops8h 15m

Chicago O'Hare Intl

Sat 10/17

4:53 pm-10:48 pm

1 stop5h 55m

$834

StillwaterChicago

SWO - ORD

SWOORD

Stillwater Searcy Fld

Wed 10/14

6:05 am-2:20 pm

2 stops8h 15m

Chicago O'Hare Intl

Sat 10/17

4:53 pm-10:48 pm

1 stop5h 55m

$859

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Stillwater to Chicago O'Hare Intl Airport

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 O'Hare Intl?

American Airlines is the most popular carrier operating from Stillwater Searcy Fld to Chicago O'Hare Intl

What airlines fly to Chicago O'Hare Intl Airport?

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Stillwater according to our data. American Airlines is the first choice among our users, with 59% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

When to book flights from Stillwater to Chicago O'Hare Intl Airport

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

Cheap Stillwater to Chicago O'Hare Intl Airport (SWO to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Stillwater to Chicago O'Hare Intl Airport

Fastest flight time

5h 54m

Direct flights

None
The fastest flight from Stillwater to Chicago O'Hare Intl Airport takes 5h 54m
There are no direct flights from Stillwater to Chicago O'Hare Intl Airport. There are no popular flight routes from Stillwater to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Stillwater to Chicago O'Hare Intl Airport

  • How far is Stillwater Searcy Fld to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 635.6 mi away from Stillwater Searcy Fld. Typically, this will take 5h 54m by plane in normal conditions.

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

    Prices for flights from Stillwater Searcy Fld Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Stillwater Searcy Fld Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek 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
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Tinley Park
Elgin
Evanston

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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