How many flights from Oklahoma City to Chicago are non-stop?

In the trailing 90 days, approximately 54.8% of flights from Oklahoma City to Chicago have been non-stop. For flights that include stopovers, the median number of stopovers observed is 2. This indicates that a significant portion of available flights on this route offer the convenience of a direct journey. Travelers have a good chance of finding a non-stop option for their trip.

How many hours is the flight from Oklahoma City to Chicago?

The typical direct flight from Oklahoma City to Chicago has a median duration of 2 hours and 20 minutes. This route covers an approximate distance of 1111 kilometers. For flights that include one stop, the median travel time is considerably longer, averaging around 6 hours and 16 minutes. Travelers prioritizing speed will find direct flights significantly reduce their journey time.

Are non-stop flights from Oklahoma City to Chicago worth the extra cost?

Historically, non-stop flights from Oklahoma City to Chicago typically come with a price premium of about 21% compared to connecting flights. The median price for a direct flight has been observed at $397, while connecting flights have a median price of $328. Non-stop options historically account for approximately 48.7% of the available flights on this route. Travelers may weigh the convenience of a direct journey against this price difference.

Flights From Oklahoma City

To Chicago

Cheap Flights from Oklahoma City to Chicago

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Oklahoma City

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Prices updated today

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Fares are subject to change and may not be available for all dates. (Data last updated Aug 31, 2026.)

Today’s best flight deals from Oklahoma City to Chicago

Explore current cheapest deals departing from Oklahoma City to Chicago

2026-10-03 – 2026-10-06
OKC - Chicago
40% AI deal score
$149
$237
Round trip
2026-11-05 – 2026-11-09
OKC - Chicago
40% AI deal score
$149
$237
Round trip
2026-10-06 – 2026-10-09
OKC - Chicago
40% AI deal score
$151
$249
Round trip
2026-11-13 – 2026-11-16
OKC - Chicago
39% AI deal score
$150
$249
Round trip
2026-10-02 – 2026-10-05
OKC - Chicago
47% AI deal score
$287
$259
Round trip
2026-10-02 – 2026-10-06
OKC - Chicago
47% AI deal score
$286
$259
Round trip
2026-12-10 – 2026-12-13
OKC - Chicago
36% AI deal score
$174
$330
Round trip
2026-09-25 – 2026-10-02
OKC - Chicago
38% AI deal score
$268
$363
Round trip
2026-09-24 – 2026-09-28
OKC - Chicago
36% AI deal score
$306
$387
Round trip
2026-09-26 – 2026-09-28
OKC - Chicago
34% AI deal score
$156
$387
Round trip

Oklahoma City to Chicago: Overview

Insights for flights from Oklahoma City to Chicago

For cheap flights from Oklahoma City to Chicago, February stands out as the most affordable month, with a median fare of just $197. January is also a strong contender, offering a median fare of $202, followed by April at $239. These months present the best opportunities for budget-conscious travelers.

Fares for flights from Oklahoma City to Chicago typically range from $330–$446, with a median price of $399. Right now, current fares are below the typical level, and about 1% of recent fares were classified as a good price. New deals appear almost daily for this route, so setting up a price alert can be beneficial.

When flying from Oklahoma City to Chicago, 54.8% of recent fares were for direct flights. This means a meaningful share are non-stop, while the remaining itineraries typically include 2 connections. You'll find a mix of options, allowing you to choose between convenience and potentially lower prices with connecting flights.

A typical journey from Oklahoma City to Chicago takes about 2h 20m, including connections. This route is considered a short-haul flight, covering a distance of 1111 kilometers. The relatively short duration makes it a convenient option for travelers looking for a quick trip between these two cities.

How much is a round trip from Oklahoma City to Chicago

Regular price: $223 - $380

Prices are currently below the regular range.

The regular price range for flights from Oklahoma City to Chicago is $223 to $380. The current lowest deal is $185 with Frontier Airlines for travel from Sep 23-Sep 29.

now $185

Low $223

High $380

The cheapest time to fly from Oklahoma City to Chicago

The cheapest month to fly from Oklahoma City to Chicago is January, with a median price of $237. The most expensive month is June, with a median price of $543. Prices are generally lower from January to December.

January

Cheapest

Flights from $237

June

Most Expensive

Flights from $543

Jan

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Oklahoma City to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from Oklahoma City to Chicago

Wed, Aug 26

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (MDW)

$607

$485

One-way

Wed, Aug 26

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (MDW)

$535

$513

One-way

Thu, Aug 27

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (ORD)

Frontier Airlines

$547

$353

One-way

Fri, Aug 28

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (MDW)

$584

$531

One-way

Thu, Sep 3

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (ORD)

Frontier Airlines

$257

$249

One-way

Thu, Sep 3

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (ORD)

Frontier Airlines

$276

$265

One-way

Biggest price drops on these dates for flights from Oklahoma City to Chicago

2 nights

Aug 27 - Aug 29

$547 → $353

35%

4 nights

Nov 3 - Nov 7

$276 → $159

42%

3 nights

Aug 26 - Aug 29

$584 → $485

17%

5 nights

Sep 10 - Sep 15

$280 → $185

34%

Popular Airports to fly from Oklahoma City to Chicago

Oklahoma City - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Oklahoma City to Chicago are below the typical level at $185.

📅 Best time to fly

Fly in February for the lowest prices.

Historically, February offers the lowest median prices at $197 for this route.

⏱️ Flight duration

Direct flights take 2h 20m.

The median flight duration for direct flights on this route is 2 hours 20 minutes.

✈️ Airlines & availability

Mixed availability of direct flights.

Direct flights are available on 54.8% of recent routes, with connecting flights having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers the best deal.

Frontier Airlines has a recent deal for $185 from Oklahoma City to Chicago.

🎯 Booking tip

Deals are frequent for this route.

Historically, deals for flights from Oklahoma City to Chicago appear frequently.

Oklahoma City main airports to depart from

Will Rogers World (OKC)

Cheapest

Will Rogers World Airport (OKC) is a convenient option for flights from Oklahoma City to Chicago.

📍 ~11 km from Oklahoma City (reachable by car)

💸 Flights from ~$160

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O Hare International is a good option for flights to Chicago, offering competitive prices from Oklahoma City.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$170

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$308

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Oklahoma City to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From OKC

Elite

Sep 11

Chicago, United States

67% AI deal score

$3,064

$2,371

Save $693

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Oct 13

Chicago, United States

66% AI deal score

$2,346

$1,937

Save $409

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Sep 29

Chicago, United States

66% AI deal score

$2,431

$2,062

Save $369

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Sep 11

Chicago, United States

66% AI deal score

$2,722

$2,308

Save $414

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Sep 11

Chicago, United States

66% AI deal score

$2,770

$2,355

Save $415

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Sep 09

Chicago, United States

66% AI deal score

$2,779

$2,405

Save $374

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Sep 09

Chicago, United States

66% AI deal score

$2,943

$2,421

Save $522

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Sep 07

Chicago, United States

66% AI deal score

$3,205

$2,692

Save $513

Alaska Airlines, Inc., +1

Business Class

From OKC

Elite

Oct 13

Chicago, United States

65% AI deal score

$2,321

$2,052

Save $269

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Sep 08

Chicago, United States

65% AI deal score

$3,203

$2,835

Save $368

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Sep 11

Chicago, United States

49% AI deal score

$2,770

$2,600

Save $170

Alaska Airlines, Inc.

Business Class

From OKC

Elite

Sep 07

Chicago, United States

49% AI deal score

$2,749

$2,619

Save $130

Alaska Airlines, Inc., +1

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Oklahoma City to Chicago is typically between 28 and 59 days prior to departure. During this period, the average price for a flight has been observed at approximately $315. Booking within 0-6 days of departure, for instance, has historically shown a higher average price of around $482. Prices generally tend to increase as the departure date approaches, particularly within the last week.

Across the trailing quarter, a good price for a flight from Oklahoma City to Chicago is considered to be $330 or less. The median price for this route over the same period was $399. Prices can vary, with 75% of observed prices being $446 or less. Travelers aiming for a more economical fare should target prices at or below the $330 threshold.

Historically, the cheapest months to fly from Oklahoma City to Chicago include February, with a median price of $197, and January, with a median price of $202. April also typically offers competitive fares, with a median price of $239. These months generally present more affordable options compared to the annual median price of $399 for this route. Travelers seeking lower fares may find these months particularly advantageous.

Related routes

More routes from Oklahoma City

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Flights to Chicago from other cities

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Oklahoma City to Chicago: Overview

Insights for flights from Oklahoma City to Chicago

How much is a round trip from Oklahoma City to Chicago

Regular price: $223 - $380

Prices are currently below the regular range.

The regular price range for flights from Oklahoma City to Chicago is $223 to $380. The current lowest deal is $185 with Frontier Airlines for travel from Sep 23-Sep 29.

now $185

Low $223

High $380

The cheapest time to fly from Oklahoma City to Chicago

January

Cheapest

Flights from $237

June

Most Expensive

Flights from $543

Jan

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Oklahoma City to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from Oklahoma City to Chicago

Wed, Aug 26

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (MDW)

$607

$485

One-way

Wed, Aug 26

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (MDW)

$535

$513

One-way

Thu, Aug 27

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (ORD)

Frontier Airlines

$547

$353

One-way

Fri, Aug 28

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (MDW)

$584

$531

One-way

Thu, Sep 3

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (ORD)

Frontier Airlines

$257

$249

One-way

Thu, Sep 3

⌛ Last-Minute

OKC - Chicago

Oklahoma City (OKC) - Chicago (ORD)

Frontier Airlines

$276

$265

One-way

Biggest price drops on these dates for flights from Oklahoma City to Chicago

2 nights

Aug 27 - Aug 29

$547 → $353

35%

4 nights

Nov 3 - Nov 7

$276 → $159

42%

3 nights

Aug 26 - Aug 29

$584 → $485

17%

5 nights

Sep 10 - Sep 15

$280 → $185

34%

Popular Airports to fly from Oklahoma City to Chicago

Oklahoma City - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Oklahoma City to Chicago are below the typical level at $185.

📅 Best time to fly

Fly in February for the lowest prices.

Historically, February offers the lowest median prices at $197 for this route.

⏱️ Flight duration

Direct flights take 2h 20m.

The median flight duration for direct flights on this route is 2 hours 20 minutes.

✈️ Airlines & availability

Mixed availability of direct flights.

Direct flights are available on 54.8% of recent routes, with connecting flights having 2 stopovers.

🏆 Airline highlight

Frontier Airlines offers the best deal.

Frontier Airlines has a recent deal for $185 from Oklahoma City to Chicago.

🎯 Booking tip

Deals are frequent for this route.

Historically, deals for flights from Oklahoma City to Chicago appear frequently.

Oklahoma City main airports to depart from

Will Rogers World (OKC)

Cheapest

Will Rogers World Airport (OKC) is a convenient option for flights from Oklahoma City to Chicago.

📍 ~11 km from Oklahoma City (reachable by car)

💸 Flights from ~$160

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O Hare International is a good option for flights to Chicago, offering competitive prices from Oklahoma City.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$170

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

Chicago, United States

49% AI deal score

$2,749

$2,619

Save $130

Alaska Airlines, Inc., +1

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Oklahoma City to Chicago

Today’s best flight deals from Oklahoma City to Chicago

Oklahoma City to Chicago: Overview

Insights for flights from Oklahoma City to Chicago

How much is a round trip from Oklahoma City to Chicago

The cheapest time to fly from Oklahoma City to Chicago

Direct flights from Oklahoma City to Chicago

Last-minute flights going from Oklahoma City to Chicago

Biggest price drops on these dates for flights from Oklahoma City to Chicago

Popular Airports to fly from Oklahoma City to Chicago

Oklahoma City - Chicago route insights

Recent fares are below the typical level.

Fly in February for the lowest prices.

Direct flights take 2h 20m.

Mixed availability of direct flights.

Frontier Airlines offers the best deal.

Deals are frequent for this route.

Oklahoma City main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 11

Oct 13

Sep 29

Sep 11

Sep 11

Sep 09

Sep 09

Sep 07

Oct 13

Sep 08

Sep 11

Sep 07

Frequently Asked Questions About Flights to Chicago

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

What is a good price for a flight from Oklahoma City to Chicago?

Which months have the cheapest flights from Oklahoma City to Chicago?

How many flights from Oklahoma City to Chicago are non-stop?

How many hours is the flight from Oklahoma City to Chicago?

Are non-stop flights from Oklahoma City to Chicago worth the extra cost?

Related routes

More routes from Oklahoma City

Flights to Chicago from other cities

Oklahoma City to Chicago: Overview

Insights for flights from Oklahoma City to Chicago

How much is a round trip from Oklahoma City to Chicago

The cheapest time to fly from Oklahoma City to Chicago

Direct flights from Oklahoma City to Chicago

Last-minute flights going from Oklahoma City to Chicago

Biggest price drops on these dates for flights from Oklahoma City to Chicago

Popular Airports to fly from Oklahoma City to Chicago

Oklahoma City - Chicago route insights

Recent fares are below the typical level.

Fly in February for the lowest prices.

Direct flights take 2h 20m.

Mixed availability of direct flights.

Frontier Airlines offers the best deal.

Deals are frequent for this route.

Oklahoma City main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Sep 11

Oct 13

Sep 29

Sep 11

Sep 11

Sep 09

Sep 09

Sep 07

Oct 13

Sep 08

Sep 11

Sep 07

Frequently Asked Questions About Flights to Chicago

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

What is a good price for a flight from Oklahoma City to Chicago?

Which months have the cheapest flights from Oklahoma City to Chicago?