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Cheap Flights from Oklahoma City Will Rogers World to Chicago

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Compare Oklahoma City Will Rogers World to Chicago flight deals

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Flight deals from Oklahoma City Will Rogers World to Chicago

Looking for a cheap last-minute deal or the best return flight from Oklahoma City Will Rogers World to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.172 € per passenger.Departing Fri, 3 Oct, returning Sun, 5 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Oklahoma City Will Rogers World on Fri, 3 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sun, 5 Oct, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From 172 €, select.
Chicago.172 € per passenger.Departing Fri, 19 Sep, returning Mon, 22 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Oklahoma City Will Rogers World on Fri, 19 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 22 Sep, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From 172 €, select.
Chicago.172 € per passenger.Departing Fri, 22 Aug, returning Sun, 24 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Oklahoma City Will Rogers World on Fri, 22 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sun, 24 Aug, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From 172 €, select.
Chicago.176 € per passenger.Departing Sat, 12 Jul, returning Sat, 19 Jul.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Oklahoma City Will Rogers World on Sat, 12 Jul, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 19 Jul, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From 176 €, select.
Chicago.182 € per passenger.Departing Thu, 31 Jul, returning Tue, 5 Aug.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Oklahoma City Will Rogers World on Thu, 31 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 5 Aug, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From 182 €, select.
Chicago.182 € per passenger.Departing Thu, 19 Jun, returning Sat, 21 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Oklahoma City Will Rogers World on Thu, 19 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 21 Jun, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From 182 €, select.
Chicago.194 € per passenger.Departing Fri, 30 May, returning Fri, 6 Jun.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Oklahoma City Will Rogers World on Fri, 30 May, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri, 6 Jun, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From 194 €, select.
Chicago.249 € per passenger.Departing Tue, 1 Jul, returning Tue, 1 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Oklahoma City Will Rogers World on Tue, 1 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 1 Jul, arriving in Oklahoma City Will Rogers World.Price includes taxes and charges.From 249 €, select.

Find the cheapest month to fly from Oklahoma City Will Rogers World to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Oklahoma City Will Rogers World to Chicago flights are currently cheapest in August.
May
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Jun
from 182 €
Jul
from 176 €
Aug
from 172 €
Sep
from 172 €
Oct
from 172 €
Nov
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Dec
from 312 €
Jan
from 312 €
Feb
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Mar
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Apr
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Direct flights from Oklahoma City Will Rogers World to Chicago

Alternative Oklahoma City Will Rogers World to Chicago routes

Looking for the cheapest, fastest or easiest route from Oklahoma City Will Rogers World to Chicago? You could fly into the following airports instead.

Oklahoma City to Chicago: Flight information

The things to know before you go.
Cheapest flight found172 €
Cheapest month to flyAugust
Average flight time2 hrs, 5 mins
Most popular airlineAlaska Airlines
Average flights per week281

Finding cheap flights from Oklahoma City Will Rogers World to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Oklahoma City Will Rogers World to Chicago is 172 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 5 minutes is the average flight time from Oklahoma City Will Rogers World to Chicago.
Alaska Airlines, American Airlines and SkyWest Airlines fly direct from Oklahoma City Will Rogers World to Chicago.
As of May 2025, there are 281 flights per week flying from Oklahoma City Will Rogers World to Chicago.
The cheapest month to fly from Oklahoma City Will Rogers World to Chicago is usually August.
If you're flying from Oklahoma City Will Rogers World Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from 172 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Oklahoma City Will Rogers World Airport to Chicago on Friday, 22 August 2025.
Yes – the average flight time is 2 hours and 5 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago.

Flying from Will Rogers World Airport (OKC) to Chicago: what you need to know

  • Around 2 hours 25 minutes is how long you can expect to be in the air on a direct flight from Will Rogers World Airport to Chicago.

  • Chicago and Oklahoma City (where Will Rogers World Airport is located) are both in the UTC-5 timezone. That means you won't have to adjust your watch after you land.

  • The most popular route is from Will Rogers World Airport (OKC) to O'Hare International Airport (ORD). Take your pick of 46 services every week between these two airports. If you'd like to get on your way as soon as you can, the earliest flight from OKC to ORD is the 05:05 American Airlines service. If you'd rather fly out later on, the last departure is at 19:22 with American Airlines.

  • Give yourself enough time to get on your OKC to Chicago flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • If you're jetting off during a bank holiday or another peak period, give yourself more time. A good general rule is two hours ahead of domestic flights and up to four hours before international departures. Security and check-in lines will be longer.

  • Begin your journey at OKC and travel nonstop to O'Hare International Airport (ORD). That will be your arrival point when searching for Will Rogers World Airport to Chicago tickets.

  • Choose from a variety of airlines that operate direct flights from Will Rogers World Airport to Chicago. Get on board with any of these:

  • OKC is around 11 kilometres from central Oklahoma City. If you're driving, catching a cab or ride-sharing from the centre, it'll take 15 minutes or so to arrive, depending on the traffic.

  • In search of a hotel close to OKC? If you're catching an early flight from Will Rogers World Airport to Chicago, these accommodation options will put you moments from check-in:

  • 81.65% of flights leaving Will Rogers World Airport touch down at their destination as planned. With its impressive on-time stats, you're unlikely to face delays when setting off from OKC.

  • OKC is located at 7100 Terminal Drive.

How to find the cheapest flights from Will Rogers World Airport (OKC) to Chicago

  • 86 € is currently the best price for a one-way Will Rogers World Airport to Chicago flight. Return plane tickets start from 172 €. These prices can change based on availability and demand.

  • To secure cheap flights from OKC to Chicago, book your trip two months ahead of your departure.

  • The best month for finding cheap Will Rogers World Airport to Chicago tickets is June. Use the 'Whole month' tool to compare all available prices, then choose the dates that offer the biggest savings.

  • You don't need to check back in every day to see if fares have dropped when you set up a Price Alert. We'll update you as soon as there's an updated deal for cheap flights from OKC to Chicago.

  • Tailor your flights with filters. Pick your ideal departure and arrival times, total journey duration and airlines. You can also sort your results by 'Best,' 'Cheapest' or 'Fastest' flights from Will Rogers World Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It'll take you around 35 minutes to reach the centre driving.

  • If you're taking public transport, expect a journey time of around 55 minutes.

  • If you're coming in on a late flight from Will Rogers World Airport to Chicago, nothing beats the convenience of staying close to the terminal. Grab your bags from the carousel and then be showered and sleeping not long after at one of these hotels near ORD:

  • Grab an O'Hare International Airport rental car and discover Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are leading providers you can book with here.

  • To get the best deal, book your vehicle from O'Hare International Airport about four weeks ahead of your flight from OKC to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Will Rogers World Airport to Chicago has hit the runway, you can reach the city centre in around 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • Public transport will get you there in about 45 minutes.

  • Hang the 'Do not disturb' sign on your door and unwind at a hotel close to MDW. Here are a few options where you can kick back after your OKC to Chicago flight:

  • Forget about public transport schedules or waiting forever for a cab. Pick up a Chicago Midway International Airport rental car and blaze your own trail. Check out the rates and availability from Dollar, Hertz and Budget.

  • Avoid paying more than you need to. Booking your ride four weeks before your arrival at MDW can land you a better rate.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Hop off your flight from Will Rogers World Airport to Chicago and make your way to your hotel or jump right into sightseeing. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 25 minutes to drive there.

  • If you go by public transport, the journey will take you around 4 hours 15 minutes.

  • If you don't want to travel to the centre, head for a hotel close to RFD. Make yourself comfy at one of these options after your OKC to Chicago flight:

  • Start your journey without stressing about how to reach your destination with a Chicago Rockford International Airport rental car. Book your wheels with reliable names here like Budget, Alamo and National.

  • If you prefer a specific kind of vehicle, booking early increases your chances of finding what you want. Secure your ride from RFD a couple of weeks ahead of your flight from Will Rogers World Airport to Chicago.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your trip dates before locking in your flight from Will Rogers World Airport to Chicago. The city buzzes during peak season, but prices are often higher and top attractions can be busy. Visit Chicago in the low season if you want a quieter vibe.

  • Before booking a Will Rogers World Airport to Chicago plane ticket, think about the weather you're most comfortable in. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • For cooler conditions, search for a cheap ticket from OKC to Chicago in January when temperatures average between -12ºC (10ºF) and 3ºC (37ºF).

More about Chicago

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be discovered once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, top sights here include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If there's time to check out another corner of United States, head for Indianapolis, about 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are the start of reasons to visit.

Plan the rest of your trip from Oklahoma City to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.