Cheap Flights from Oklahoma City to Chicago
Browse current best options from Oklahoma City. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Oklahoma City
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
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 Oklahoma City to Chicago
Explore current cheapest deals departing from Oklahoma City to Chicago
Round trip
Sort by: Cheapest
November 10 - November 17
OKC - Chicago
$309
$179
Round trip
October 14 - October 20
OKC - Chicago
$308
$191
Round trip
October 13 - October 20
OKC - Chicago
$308
$193
Round trip
October 4 - October 20
OKC - Chicago
$281
$194
Round trip
November 10 - November 16
OKC - Chicago
$309
$199
Round trip
October 1 - October 7
OKC - Chicago
$306
$227
Round trip
September 16 - September 23
OKC - Chicago
$161
$229
Round trip
August 8 - August 18
OKC - Chicago
$241
$230
Round trip
August 18 - August 23
OKC - Chicago
$282
$252
Round trip
September 12 - September 16
OKC - Chicago
$168
$253
Round trip
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Route Intelligence — 486,190 Searches this Week
Insights for flights from Oklahoma City to Chicago
How much is a round trip from Oklahoma City to Chicago
Regular price: $261 - $376
Prices for flights from Oklahoma City to Chicago are currently below the regular range.
The regular price range for flights from Oklahoma City to Chicago is between $261 and $376. The current lowest deal is $179 with Frontier Airlines, for travel from Nov 10-Nov 17.
now $179
Low $261
High $376
The cheapest time to fly from Oklahoma City to Chicago
The cheapest month to fly from Oklahoma City to Chicago is February, with a median price of $197. The most expensive month is June, with a median price of $451. Prices are generally lower from January to December.
February
Flights from $197
June
Flights from $451
Direct flights from Oklahoma City to Chicago
American Airlines
Southwest Airlines
Last-minute flights going from Oklahoma City to Chicago
Wed, Jul 1
OKC - Chicago
Oklahoma City (OKC) - Chicago (MDW)
Southwest Airlines
$322
$331
One-way
Thu, Jul 2
OKC - Chicago
Oklahoma City (OKC) - Chicago (ORD)
Frontier Airlines
$299
$264
One-way
Fri, Jul 3
OKC - Chicago
Oklahoma City (OKC) - Chicago (MDW)
$512
$407
One-way
Sun, Jul 5
OKC - Chicago
Oklahoma City (OKC) - Chicago (MDW)
$507
$477
One-way
Mon, Jul 6
OKC - Chicago
Oklahoma City (OKC) - Chicago (ORD)
Deutsche Luft Hansa
$312
$378
One-way
Tue, Jul 7
OKC - Chicago
Oklahoma City (OKC) - Chicago (ORD)
$298
$321
One-way
Biggest price drops on these dates for flights from Oklahoma City to Chicago
Nov 10 - Nov 17
$309 → $179
42%
Oct 14 - Oct 20
$308 → $191
38%
Jul 22 - Jul 26
$474 → $357
25%
Oct 13 - Oct 20
$308 → $193
37%
Popular Airports to fly from Oklahoma City to Chicago
Oklahoma City - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares for flights from Oklahoma City to Chicago are above the typical level, with a median price of $356.
📅 Best time to fly
February is historically cheapest at $197
Historically, February is the cheapest month to fly from Oklahoma City to Chicago, with a median price of $197.
⏱️ Flight duration
Median flight time is 5h 23m
The median flight time from Oklahoma City to Chicago is 5 hours and 23 minutes.
✈️ Airlines & availability
Mixed availability of direct flights
Approximately 48.7% of recent deals are for direct flights, with connecting flights typically having 2 stopovers.
🏆 Airline highlight
American Airlines offers direct flights
American Airlines is one of the carriers offering direct flights on the Oklahoma City to Chicago route.
🎯 Booking tip
Deals are frequent for this route
Deals for flights from Oklahoma City to Chicago are frequent, with over 1 deal per day historically.
Oklahoma City main airports to depart from
Will Rogers World (OKC)
Will Rogers World Airport offers flights from Oklahoma City to Chicago, with competitive pricing for your journey.
📍 ~10 km from Oklahoma City center (reachable by car)
💸 Flights from ~$179
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub for flights to Chicago from Oklahoma City.
📍 ~25 km from city center (reachable by car or public transport)
💸 Flights from ~$179
Chicago Midway International (MDW)
Chicago Midway International Airport offers another convenient option for flights from Oklahoma City.
📍 ~15 km from city center (reachable by car or public transport)
💸 Flights from ~$229
Chicago Rockford International (RFD)
Chicago Rockford International Airport is an alternative arrival airport for flights to the Chicago area.
📍 ~120 km from city center (reachable by car)
💸 Flights from ~$232
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with frequent flight options and direct rail access.
📍 ~135 km from destination city (reachable by car, train)
💸 Flights from ~$303
South Bend International (SBN)
South Bend International is the closest alternative to Chicago, with direct commuter rail to downtown.
📍 ~120 km from destination city (reachable by car, train)
💸 Flights from ~$241
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, good for travelers on Chicago's eastern side.
📍 ~230 km from destination city (reachable by car)
💸 Flights from ~$248
Dane County Regional (MSN)
Dane County Regional is a reliable, less congested alternative to Chicago or Milwaukee airports.
📍 ~220 km from destination city (reachable by car)
💸 Flights from ~$299
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service, useful for southeastern Chicago suburbs.
📍 ~240 km from destination city (reachable by car)
💸 Flights from ~$309
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
Aug 22
Chicago, United States
80% AI deal score
$1,415
$696
Save $719
From OKC
Elite
Sep 11
Chicago, United States
77% AI deal score
$1,128
$689
Save $439
From OKC
Elite
Aug 13
Chicago, United States
73% AI deal score
$1,097
$689
Save $408
From OKC
Elite
Oct 21
Chicago, United States
68% AI deal score
$2,353
$1,781
Save $572
From OKC
Elite
Jul 14
Chicago, United States
68% AI deal score
$706
$601
Save $105
From OKC
Elite
Aug 12
Chicago, United States
68% AI deal score
$725
$583
Save $142
From OKC
Elite
Aug 27
Chicago, United States
68% AI deal score
$746
$599
Save $147
From OKC
Elite
Aug 24
Chicago, United States
68% AI deal score
$739
$599
Save $140
From OKC
Elite
Dec 03
Chicago, United States
67% AI deal score
$2,274
$1,826
Save $448
From OKC
Elite
Jul 27
Chicago, United States
67% AI deal score
$2,309
$1,832
Save $477
From OKC
Elite
Oct 06
Chicago, United States
67% AI deal score
$2,318
$1,892
Save $426
From OKC
Elite
Nov 03
Chicago, United States
67% AI deal score
$724
$609
Save $115
From OKC
Elite
Aug 07
Chicago, United States
67% AI deal score
$803
$693
Save $110
From OKC
Elite
Sep 19
Chicago, United States
67% AI deal score
$703
$599
Save $104
From OKC
Elite
Jul 27
Chicago, United States
66% AI deal score
$2,225
$1,832
Save $393
From OKC
Elite
Jul 17
Chicago, United States
66% AI deal score
$2,207
$1,898
Save $309
From OKC
Elite
Jul 17
Chicago, United States
66% AI deal score
$2,207
$1,898
Save $309
From OKC
Elite
Aug 27
Chicago, United States
66% AI deal score
$776
$687
Save $89
From OKC
Elite
Sep 05
Chicago, United States
66% AI deal score
$699
$599
Save $100
From OKC
Elite
Aug 28
Chicago, United States
66% AI deal score
$737
$658
Save $79
From OKC
Elite
Aug 27
Chicago, United States
66% AI deal score
$755
$669
Save $86
From OKC
Elite
Aug 21
Chicago, United States
66% AI deal score
$768
$675
Save $93
From OKC
Elite
Aug 27
Chicago, United States
65% AI deal score
$675
$617
Save $58
From OKC
Elite
Aug 11
Chicago, United States
65% AI deal score
$747
$583
Save $164
From OKC
Elite
Aug 11
Chicago, United States
65% AI deal score
$747
$583
Save $164
From OKC
Elite
Aug 12
Chicago, United States
65% AI deal score
$747
$583
Save $164
From OKC
Elite
Aug 12
Chicago, United States
65% AI deal score
$747
$583
Save $164
From OKC
Elite
Jul 14
Chicago, United States
65% AI deal score
$616
$583
Save $33
From OKC
Elite
Aug 10
Chicago, United States
65% AI deal score
$747
$591
Save $156
From OKC
Elite
Aug 10
Chicago, United States
65% AI deal score
$752
$591
Save $161
From OKC
Elite
Aug 11
Chicago, United States
65% AI deal score
$747
$591
Save $156
From OKC
Elite
Aug 11
Chicago, United States
65% AI deal score
$752
$591
Save $161
From OKC
Elite
Aug 12
Chicago, United States
65% AI deal score
$747
$591
Save $156
From OKC
Elite
Aug 12
Chicago, United States
65% AI deal score
$747
$591
Save $156
From OKC
Elite
Aug 13
Chicago, United States
65% AI deal score
$747
$591
Save $156
From OKC
Elite
Sep 17
Chicago, United States
65% AI deal score
$700
$637
Save $63
From OKC
Elite
Jun 23
Chicago, United States
50% AI deal score
$2,545
$2,318
Save $227
From OKC
Elite
Oct 06
Chicago, United States
50% AI deal score
$647
$601
Save $46
From OKC
Elite
Aug 28
Chicago, United States
50% AI deal score
$782
$725
Save $57
From OKC
Elite
Aug 11
Chicago, United States
50% AI deal score
$745
$591
Save $154
From OKC
Elite
Aug 12
Chicago, United States
50% AI deal score
$745
$591
Save $154
From OKC
Elite
Aug 15
Chicago, United States
50% AI deal score
$745
$591
Save $154
From OKC
Elite
Aug 15
Chicago, United States
50% AI deal score
$745
$591
Save $154
From OKC
Elite
Aug 10
Chicago, United States
50% AI deal score
$747
$599
Save $148
From OKC
Elite
Aug 10
Chicago, United States
50% AI deal score
$747
$599
Save $148
From OKC
Elite
Aug 10
Chicago, United States
50% AI deal score
$753
$599
Save $154
From OKC
Elite
Aug 13
Chicago, United States
50% AI deal score
$745
$599
Save $146
From OKC
Elite
Aug 13
Chicago, United States
50% AI deal score
$747
$599
Save $148
From OKC
Elite
Aug 15
Chicago, United States
50% AI deal score
$747
$599
Save $148
From OKC
Elite
Aug 24
Chicago, United States
50% AI deal score
$725
$669
Save $56
From OKC
Elite
Jun 19
Chicago, United States
49% AI deal score
$2,495
$2,373
Save $122
From OKC
Elite
Aug 29
Chicago, United States
49% AI deal score
$689
$655
Save $34
From OKC
Elite
Aug 14
Chicago, United States
49% AI deal score
$1,097
$847
Save $250
From OKC
Elite
Aug 12
Chicago, United States
49% AI deal score
$1,097
$868
Save $229
From OKC
Elite
Aug 13
Chicago, United States
49% AI deal score
$741
$599
Save $142
From OKC
Elite
Aug 15
Chicago, United States
49% AI deal score
$738
$599
Save $139
From OKC
Elite
Aug 15
Chicago, United States
49% AI deal score
$741
$599
Save $142
From OKC
Elite
Aug 11
Chicago, United States
49% AI deal score
$752
$629
Save $123
From OKC
Elite
Aug 12
Chicago, United States
49% AI deal score
$752
$629
Save $123
From OKC
Elite
Sep 04
Chicago, United States
49% AI deal score
$699
$658
Save $41
From OKC
Elite
Aug 07
Chicago, United States
49% AI deal score
$739
$707
Save $32
From OKC
Elite
Oct 21
Chicago, United States
48% AI deal score
$626
$610
Save $16
From OKC
Elite
Jul 14
Chicago, United States
48% AI deal score
$634
$629
Save $5
From OKC
Elite
Jul 15
Chicago, United States
48% AI deal score
$686
$679
Save $7
From OKC
Elite
Jul 12
Chicago, United States
48% AI deal score
$697
$687
Save $10
From OKC
Elite
Dec 02
Chicago, United States
48% AI deal score
$1,364
$1,107
Save $257
From OKC
Elite
Aug 14
Chicago, United States
48% AI deal score
$745
$629
Save $116
From OKC
Elite
Aug 14
Chicago, United States
48% AI deal score
$747
$629
Save $118
From OKC
Elite
Aug 16
Chicago, United States
48% AI deal score
$741
$629
Save $112
From OKC
Elite
Aug 16
Chicago, United States
48% AI deal score
$745
$629
Save $116
From OKC
Elite
Aug 10
Chicago, United States
48% AI deal score
$753
$637
Save $116
From OKC
Elite
Aug 13
Chicago, United States
48% AI deal score
$747
$637
Save $110
From OKC
Elite
Aug 14
Chicago, United States
48% AI deal score
$739
$637
Save $102
From OKC
Elite
Aug 14
Chicago, United States
48% AI deal score
$745
$637
Save $108
From OKC
Elite
Aug 14
Chicago, United States
48% AI deal score
$747
$637
Save $110
From OKC
Elite
Aug 15
Chicago, United States
48% AI deal score
$747
$637
Save $110
From OKC
Elite
Aug 16
Chicago, United States
48% AI deal score
$738
$637
Save $101
From OKC
Elite
Aug 16
Chicago, United States
48% AI deal score
$739
$637
Save $102
From OKC
Elite
Aug 16
Chicago, United States
48% AI deal score
$745
$637
Save $108
From OKC
Elite
Sep 10
Chicago, United States
48% AI deal score
$693
$669
Save $24
From OKC
Elite
Sep 04
Chicago, United States
47% AI deal score
$676
From OKC
Elite
Sep 10
Chicago, United States
47% AI deal score
$687
From OKC
Elite
Jul 13
Chicago, United States
47% AI deal score
$704
From OKC
Elite
Jun 30
Chicago, United States
47% AI deal score
$708
From OKC
Elite
Jul 17
Chicago, United States
47% AI deal score
$725
From OKC
Elite
Jul 09
Chicago, United States
47% AI deal score
$736
From OKC
Elite
Jul 14
Chicago, United States
47% AI deal score
$612
From OKC
Elite
Jul 14
Chicago, United States
47% AI deal score
$629
From OKC
Elite
Jul 17
Chicago, United States
47% AI deal score
$658
From OKC
Elite
Aug 11
Chicago, United States
47% AI deal score
$747
$661
Save $86
From OKC
Elite
Aug 12
Chicago, United States
47% AI deal score
$745
$661
Save $84
From OKC
Elite
Jul 15
Chicago, United States
47% AI deal score
$661
From OKC
Elite
Jul 29
Chicago, United States
47% AI deal score
$666
From OKC
Elite
Aug 10
Chicago, United States
47% AI deal score
$747
$669
Save $78
From OKC
Elite
Sep 03
Chicago, United States
47% AI deal score
$793
From OKC
Elite
Jul 30
Chicago, United States
46% AI deal score
$725
From OKC
Elite
Jul 30
Chicago, United States
46% AI deal score
$725
From OKC
Elite
Aug 08
Chicago, United States
46% AI deal score
$1,398
$1,218
Save $180
From OKC
Elite
Aug 13
Chicago, United States
46% AI deal score
$745
$669
Save $76
From OKC
Elite
Aug 15
Chicago, United States
46% AI deal score
$739
$669
Save $70