
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Frontier) |
One-way from | $65 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $410 |
Good round-trip deal | $386 or less |
Good one-way deal | $223 or less |
Fly from
Fly to
Route
Depart
Return
Oklahoma CityChicago
OKC - MDW
OKCMDW
Oklahoma City Will Rogers World
Wed 5/6
4:50 pm-9:45 pm
1 stop4h 55m
Chicago Midway
Wed 5/13
9:05 pm-11:15 pm
Nonstop2h 10m
Oklahoma CityChicago
OKC - MDW
OKCMDW
Oklahoma City Will Rogers World
Wed 4/22
4:50 pm-9:45 pm
1 stop4h 55m
Chicago Midway
Wed 4/29
10:20 am-12:30 pm
Nonstop2h 10m
Oklahoma CityChicago
OKC - ORD
OKCORD
Oklahoma City Will Rogers World
Wed 6/3
5:29 pm-12:08 am
1 stop6h 39m
Chicago O'Hare Intl
Wed 6/10
6:30 am-11:16 am
1 stop4h 46m
Oklahoma CityChicago
OKC - MDW
OKCMDW
Oklahoma City Will Rogers World
Wed 5/6
3:05 pm-4:55 pm
Nonstop1h 50m
Chicago Midway
Sat 5/9
10:15 am-8:05 pm
2 stops9h 50m
Oklahoma CityChicago
OKC - MDW
OKCMDW
Oklahoma City Will Rogers World
Tue 4/28
11:26 am-4:26 pm
1 stop5h 00m
Chicago Midway
Thu 4/30
10:41 am-5:04 pm
1 stop6h 23m
Oklahoma CityChicago
OKC - ORD
OKCORD
Oklahoma City Will Rogers World
Sat 4/18
1:44 pm-4:03 pm
Nonstop2h 19m
Chicago O'Hare Intl
Mon 4/20
12:58 pm-3:35 pm
Nonstop2h 37m
Oklahoma CityChicago
OKC - MDW
OKCMDW
Oklahoma City Will Rogers World
Sat 5/2
5:00 am-6:50 am
Nonstop1h 50m
Chicago Midway
Mon 5/4
10:05 pm-12:15 am
Nonstop2h 10m
Oklahoma CityChicago
OKC - ORD
OKCORD
Oklahoma City Will Rogers World
Sat 4/18
7:20 am-2:30 pm
1 stop7h 10m
Chicago O'Hare Intl
Tue 4/21
6:15 am-4:05 pm
1 stop9h 50m
Oklahoma CityChicago
OKC - MDW
OKCMDW
Oklahoma City Will Rogers World
Mon 6/1
3:40 pm-9:00 pm
1 stop5h 20m
Chicago Midway
Thu 6/4
10:10 am-12:15 pm
Nonstop2h 05m
Oklahoma CityChicago
OKC - MDW
OKCMDW
Oklahoma City Will Rogers World
Sat 4/18
12:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
Mon 4/20
10:05 pm-12:15 am
Nonstop2h 10m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
To ensure you get the cheapest price possible for a flight from Oklahoma City to Chicago, you should look to book at least 48 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Currently, January is the cheapest month in which you can book a flight from Oklahoma City to Chicago (average of $133). Flying from Oklahoma City to Chicago in November is currently the most expensive (average of $298). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
One of the essential ways to save on airfare from Oklahoma City to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 28% on airfare.
Travelers seeking maximum savings on their Oklahoma City to Chicago flight should consider departing on Saturday mornings when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from OKC to CHI are scheduled on a Friday (27 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (11 on average).
Atlanta (ATL) – chosen by Cheapflights users on 50% of 1-stop itineraries from Oklahoma City to Chicago on Cheapflights.
Atlanta (ATL) is the most affordable 1-stop option, with an average round-trip price of $313.
Flights via Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 14m.
Flights via Denver (DEN) offer the fastest connection on this route, with an average layover time of 3h 04m.
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
Food
Overall
Entertainment
Comfort
Crew
Boarding
Reviews
Dominic,Mar 2026
MCO - SMF
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$188 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$240 | Average$393 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$243 | Average$400 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$248 | Average$364 | FlexibilityNo cancel fee | On-time71% |