To Chicago

Cheap Flights from Tulsa to Chicago

Browse current best options from Tulsa. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Tulsa

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Prices updated 24 days ago

486,190 searches this week

171 airlines compared

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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Tulsa to Chicago

Explore current cheapest deals departing from Tulsa to Chicago

Round trip

Sort by: Cheapest

July 22 - July 29

Cheapest

TUL - Chicago

$165

$217

Round trip

September 15 - September 23

Cheapest

TUL - Chicago

$207

$217

Round trip

October 6 - October 14

Cheapest

TUL - Chicago

$190

$217

Round trip

July 14 - July 21

Cheapest

Best

TUL - Chicago

$274

$217

Round trip

July 15 - July 29

Cheapest

TUL - Chicago

$155

$217

Round trip

July 22 - July 29

Cheapest

TUL - Chicago

$167

$217

Round trip

July 29 - August 12

Cheapest

TUL - Chicago

$152

$217

Round trip

July 15 - July 29

TUL - Chicago

$150

$218

Round trip

July 7 - July 14

Earliest

TUL - Chicago

$174

$218

Round trip

August 11 - August 17

TUL - Chicago

$173

$232

Round trip

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Route Intelligence — 486,190 Searches this Week

Insights for flights from Tulsa to Chicago

A typical journey from Tulsa to Chicago takes about 5h 51m, including connections. This duration accounts for the fact that a meaningful share of itineraries involve at least one stopover. The total distance covered on this route is 938 kilometers, classifying it as a short-haul flight.

For those seeking cheap flights from Tulsa to Chicago, prices are currently above the typical level. Fares for this route typically range from $234–$621, with a median of $317. Right now, only 2% of recent fares are classified as a good price, indicating that current prices are higher than usual.

The cheapest time to fly from Tulsa to Chicago is often during specific months. February stands out as the most affordable, with a median fare of just $166. Other cost-effective months include May, where the median fare is $241, and September, with a median fare of $297.

When flying from Tulsa to Chicago, a meaningful share of itineraries are non-stop, while the rest connect once. Approximately 44.5% of recent fares for this route are direct flights from Tulsa to Chicago. For itineraries that include connections, travelers typically encounter 3 stopovers before reaching their destination. New deals for this route appear almost daily, suggesting frequent opportunities to find competitive prices.

How much is a round trip from Tulsa to Chicago

Regular price: $134 - $300

Prices for flights from Tulsa to Chicago are currently within the regular range.

The regular price range for flights from Tulsa to Chicago is between $134 and $300. The current lowest deal is $217 with American Airlines, for travel from Jul 22-Jul 29.

now $217

Low $134

High $300

The cheapest time to fly from Tulsa to Chicago

The cheapest month to fly from TUL to CHI is February, with a median price of $166. The most expensive month is December, with a median price of $872. Prices are generally lower from February to November.

February

Cheapest

Flights from $166

December

Most Expensive

Flights from $872

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Tulsa to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from Tulsa to Chicago

Fri, Jul 3

⌛ Last-Minute

TUL - Chicago

Tulsa (TUL) - Chicago (ORD)

$298

$313

One-way

Fri, Jul 3

⌛ Last-Minute

TUL - Chicago

Tulsa (TUL) - Chicago (ORD)

Deutsche Luft Hansa

$296

$390

One-way

Tue, Jul 7

⌛ Last-Minute

TUL - Chicago

Tulsa (TUL) - Chicago (MDW)

Southwest Airlines

$174

$218

One-way

Tue, Jul 7

⌛ Last-Minute

TUL - Chicago

Tulsa (TUL) - Chicago (ORD)

United Airlines

$152

$297

One-way

Wed, Jul 8

⌛ Last-Minute

TUL - Chicago

Tulsa (TUL) - Chicago (ORD)

$280

$297

One-way

Wed, Jul 8

⌛ Last-Minute

TUL - Chicago

Tulsa (TUL) - Chicago (ORD)

$280

$297

One-way

Biggest price drops on these dates for flights from Tulsa to Chicago

14 nights

Oct 20 - Nov 3

$385 → $237

38%

3 nights

Sep 26 - Sep 29

$384 → $252

34%

4 nights

Oct 19 - Oct 23

$430 → $334

22%

5 nights

Aug 17 - Aug 22

$344 → $267

22%

Popular Airports to fly from Tulsa to Chicago

Tulsa - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from Tulsa to Chicago are above the typical level, with a median price of $317.

📅 Best time to fly

February is historically the cheapest month to fly.

Historically, February is the cheapest month to fly from Tulsa to Chicago, with a median price of $166.

⏱️ Flight duration

Flights typically take 5h 51m.

The median flight duration from Tulsa to Chicago is 5 hours and 51 minutes.

✈️ Airlines & availability

A mix of direct and connecting flights are available.

Approximately 44.5% of recent deals are for direct flights from Tulsa to Chicago.

🏆 Airline highlight

American Airlines offers deals for this route.

American Airlines is one of the carriers that has offered deals on this route recently.

🎯 Booking tip

Deals appear frequently for this route.

Historically, deals for flights from Tulsa to Chicago appear frequently, averaging 1.03 deals per day.

Tulsa main airports to depart from

Tulsa International (TUL)

Cheapest

Tulsa International Airport is a good option for flights from Tulsa to Chicago.

📍 ~10 km from city center (reachable by car)

💸 Flights from ~$217

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient option for flights from Tulsa to Chicago, offering competitive pricing.

📍 ~13 km from Chicago city center (reachable by car or public transport).

💸 Flights from ~$217

Chicago Rockford International (RFD)

Chicago Rockford International serves as an alternative arrival airport for flights from Tulsa to Chicago.

📍 ~120 km from Chicago city center (reachable by car).

💸 Flights from ~$281

O Hare International (ORD)

O Hare International is a major hub for flights from Tulsa to Chicago, providing extensive connectivity.

📍 ~27 km from Chicago city center (reachable by car or public transport).

💸 Flights from ~$217

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Consider this airport for its excellent proximity to Chicago and high-frequency flight options.

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

💸 Flights from ~$303

South Bend International (SBN)

Cheapest

This airport is a good alternative due to its close proximity and direct rail connection to Chicago.

📍 ~125 km from Chicago (reachable by car or train)

💸 Flights from ~$240

Gerald R. Ford International (GRR)

This major regional hub offers a wide range of cabin classes and reliable service for travelers.

📍 ~205 km from Chicago (reachable by car)

💸 Flights from ~$242

Dane County Regional (MSN)

Choose this reliable regional airport for consistent service and less congestion than major hubs.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$278

Fort Wayne International (FWA)

This airport provides stable regional service and is an alternative for southeastern Chicago suburbs.

📍 ~230 km from Chicago (reachable by car)

💸 Flights from ~$275

Business & First Class Flight Deals to Chicago

47% AI deal score

$2,935

From TUL

Elite

Jul 21

Chicago, United States

47% AI deal score

$586

$575

Save $11

From TUL

Elite

Jul 14

Chicago, United States

47% AI deal score

$586

$575

Save $11

From TUL

Elite

Jul 15

Chicago, United States

47% AI deal score

$592

$581

Save $11

From TUL

Elite

Jul 27

Chicago, United States

47% AI deal score

$607

$596

Save $11

From TUL

Elite

Sep 25

Chicago, United States

47% AI deal score

Chicago, United States

45% AI deal score

Chicago, United States

31% AI deal score

$2,877

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Tulsa to Chicago is typically 28-59 days before departure. During this period, the average price for a ticket is around $388. Prices tend to be higher for last-minute bookings, with flights purchased 0-6 days out averaging $603. Conversely, booking more than 60 days in advance also shows higher average prices, at approximately $523.

Across the trailing quarter, a good price for a flight from Tulsa to Chicago is considered to be $234 or less. The median price for this route historically stands at $317. About 25% of all observed prices for this route were $234 or below. Prices can go significantly higher, with 75% of fares being $621 or less.

Historically, February has been the cheapest month to fly from Tulsa to Chicago, with a median price of $166. May also offers competitive prices, with a median of $241. While September is listed as the most expensive month with a median of $297, the annual median price for this route is $317, indicating that these months generally offer better value.

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