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Cheap flights from Oklahoma to Chicago from $54

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Oklahoma to Chicago departing on 4/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
7:18 am - 7:11 pm
DFW
-
ORD
11h 53m
1 stop
Multiple Airlines Logo
4:28 pm - 7:29 pm
ORD
-
DFW
3h 01mnonstop
$81Multiple Airlines
Wed, Mar 4 - Wed, Mar 11
Frontier Logo
8:55 pm - 11:13 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
5:11 pm - 8:00 pm
MDW
-
DFW
2h 49mnonstop
$81Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
10:17 pm - 12:52 am
DFW
-
ORD
2h 35mnonstop
Frontier Logo
5:11 am - 8:00 am
ORD
-
DFW
2h 49mnonstop
$82Frontier
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
8:03 pm - 10:21 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
4:09 pm - 7:03 pm
MDW
-
DFW
2h 54mnonstop
$82Frontier
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
9:48 pm - 12:21 am
DFW
-
ORD
2h 33mnonstop
Multiple Airlines Logo
8:16 pm - 9:58 am
ORD
-
DFW
13h 42m
1 stop
$87Multiple Airlines
Sat, Mar 7 - Mon, Mar 9
American Airlines Logo
7:32 pm - 9:31 pm
XNA
-
ORD
1h 59mnonstop
American Airlines Logo
7:20 am - 9:20 am
ORD
-
XNA
2h 00mnonstop
$209American Airlines
Fri, Mar 13 - Mon, Mar 16
Delta Logo
11:46 am - 6:40 pm
XNA
-
MDW
6h 54m
1 stop
Delta Logo
1:10 pm - 5:06 pm
MDW
-
XNA
3h 56m
1 stop
$229Delta
Sat, Apr 4 - Fri, Apr 10
Delta Logo
11:46 am - 5:53 pm
XNA
-
ORD
6h 07m
1 stop
Delta Logo
5:30 am - 12:07 pm
ORD
-
XNA
6h 37m
1 stop
$229Delta
Sat, Apr 4 - Sat, Apr 11
American Airlines Logo
7:32 pm - 9:31 pm
XNA
-
ORD
1h 59mnonstop
American Airlines Logo
6:22 pm - 12:08 am
ORD
-
XNA
5h 46m
1 stop
$239American Airlines
Fri, Feb 27 - Mon, Mar 2
United Airlines Logo
2:20 pm - 4:25 pm
TUL
-
ORD
2h 05mnonstop
United Airlines Logo
3:40 pm - 5:56 pm
ORD
-
TUL
2h 16mnonstop
$249United Airlines
Wed, Feb 25 - Sat, Feb 28

Frontier flights from Oklahoma to Chicago

Our best Frontier deals on Oklahoma to Chicago flight tickets
Frontier
Apr 9
DFW8:55 pmDallas/Fort Worth
2h 18m
MDW11:13 pmChicago Midway
Apr 13
MDW5:11 pmChicago Midway
2h 49m
DFW8:00 pmDallas/Fort Worth
$81
Frontier
Apr 16
DFW10:17 pmDallas/Fort Worth
2h 35m
ORD12:52 amChicago O'Hare Intl
Apr 20
ORD5:11 amChicago O'Hare Intl
2h 49m
DFW8:00 amDallas/Fort Worth
$82
Frontier
Mar 7
DFW9:48 pmDallas/Fort Worth
2h 33m
ORD12:21 amChicago O'Hare Intl
Mar 10
ORD4:28 pmChicago O'Hare Intl
3h 01m
DFW7:29 pmDallas/Fort Worth
$85

American Airlines flights from Oklahoma to Chicago

Our best American Airlines deals on Oklahoma to Chicago flight tickets
American Airlines
Mar 13
XNA7:32 pmFayetteville Northwest Arkansas
1h 59m
ORD9:31 pmChicago O'Hare Intl
Mar 16
ORD7:20 amChicago O'Hare Intl
2h 00m
XNA9:20 amFayetteville Northwest Arkansas
$209
American Airlines
Feb 27
XNA6:21 amFayetteville Northwest Arkansas
2h 04m
ORD8:25 amChicago O'Hare Intl
Mar 2
ORD6:22 pmChicago O'Hare Intl
5h 46m
1 stop
XNA12:08 amFayetteville Northwest Arkansas
$239
American Airlines
Feb 28
XNA5:00 amFayetteville Northwest Arkansas
4h 45m
1 stop
ORD9:45 amChicago O'Hare Intl
Mar 1
ORD7:31 amChicago O'Hare Intl
2h 00m
XNA9:31 amFayetteville Northwest Arkansas
$240

momondo Fare Finder

 
Customize your flight search to find flights from Oklahoma 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 7, 2026.
Use the filters below to find and compare flights from Oklahoma to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Wed 3/4

7:18 am-7:11 pm

1 stop11h 53m

Chicago O'Hare Intl

Wed 3/11

4:28 pm-7:29 pm

Nonstop3h 01m

$81

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 4/9

8:55 pm-11:13 pm

Nonstop2h 18m

Chicago Midway

Mon 4/13

5:11 pm-8:00 pm

Nonstop2h 49m

$81

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Thu 4/16

10:17 pm-12:52 am

Nonstop2h 35m

Chicago O'Hare Intl

Mon 4/20

5:11 am-8:00 am

Nonstop2h 49m

$82

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 4/16

8:03 pm-10:21 pm

Nonstop2h 18m

Chicago Midway

Mon 4/20

4:09 pm-7:03 pm

Nonstop2h 54m

$82

DallasChicago

DFW - ORD

DFWORD

Dallas/Fort Worth

Sat 3/7

9:48 pm-12:21 am

Nonstop2h 33m

Chicago O'Hare Intl

Mon 3/9

8:16 pm-9:58 am

1 stop13h 42m

$87

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Fri 3/13

7:32 pm-9:31 pm

Nonstop1h 59m

Chicago O'Hare Intl

Mon 3/16

7:20 am-9:20 am

Nonstop2h 00m

$209

FayettevilleChicago

XNA - MDW

XNAMDW

Fayetteville Northwest Arkansas

Sat 4/4

11:46 am-6:40 pm

1 stop6h 54m

Chicago Midway

Fri 4/10

1:10 pm-5:06 pm

1 stop3h 56m

$229

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Sat 4/4

11:46 am-5:53 pm

1 stop6h 07m

Chicago O'Hare Intl

Sat 4/11

5:30 am-12:07 pm

1 stop6h 37m

$229

FayettevilleChicago

XNA - ORD

XNAORD

Fayetteville Northwest Arkansas

Fri 2/27

7:32 pm-9:31 pm

Nonstop1h 59m

Chicago O'Hare Intl

Mon 3/2

6:22 pm-12:08 am

1 stop5h 46m

$239

TulsaChicago

TUL - ORD

TULORD

Tulsa

Wed 2/25

2:20 pm-4:25 pm

Nonstop2h 05m

Chicago O'Hare Intl

Sat 2/28

3:40 pm-5:56 pm

Nonstop2h 16m

$249

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Oklahoma 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 month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Oklahoma, with most prices found around $264. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Oklahoma to Chicago during January average around $322.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $528. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Oklahoma to Chicago for around $797.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Oklahoma to Chicago during this time can be as low as $520. In contrast, the most expensive time of day to depart to Chicago is in the evening when prices are around $941.

What is the cheapest Oklahoma to Chicago flight route?

Fly from Oklahoma City Will Rogers World to Chicago Midway for the best Oklahoma - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Oklahoma when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $374 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Oklahoma for as low as $304 on momondo.

What cabin class options are available on Oklahoma to Chicago flights?

There are 4 cabin classes available to choose from on Oklahoma to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Oklahoma to Chicago flights?

You could potentially save up to 13% on your flight if you consider stops on a Oklahoma to Chicago flight.

Cheap Oklahoma to Chicago flight deals and tips

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

Best Price Found

$185

Fastest flight time

1h 40m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Oklahoma in the past 72 hours is $185. The best round-trip flight deal from Oklahoma to Chicago found on momondo in the last 72 hours is $343.
The fastest flight from Oklahoma to Chicago takes 1h 40m
Direct flights go from Oklahoma to Chicago every day.
There are 3 airports in Chicago. From Oklahoma there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

  • When did momondo last update prices for flights from Oklahoma to Chicago?

    Prices for flights from Oklahoma to Chicago were last updated today.

  • How many operators does momondo search for flights from Oklahoma to Chicago?

  • How old do you have to be to fly from Oklahoma 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 Oklahoma to Chicago.

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

    The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Oklahoma to Chicago?

Best airlines flying from Oklahoma to Chicago

Compare and see reviews for airlines that fly from Oklahoma to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $138Free CancellationRating
5.7
3,054 reviews
Search Frontier flights
United AirlinesPriceFrom $182Free CancellationRating
7.4
9,245 reviews
Search United Airlines flights
American AirlinesPriceFrom $189Free CancellationRating
7.2
11,248 reviews
Search American Airlines flights
SouthwestPriceFrom $197Free CancellationRating
8.0
4,280 reviews
Search Southwest flights

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 Oklahoma to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Oklahoma.

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

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

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

Once you have performed a search for Oklahoma to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Oklahoma to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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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