Cheap Flights from Cape Girardeau (CGI) to Chicago (MDW)

Popular airlines from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago Midway Airport (MDW)

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $139
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $139

Frequently asked questions

How much does a flight from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights and cheap return flights CGI to MDW with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when CGI to MDW ticket fares go up or down.
What is the cheapest month to fly from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from CGI to MDW is when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.)?
Enter CGI to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
What is the earliest flight from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from CGI to MDW. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
Can you fly business or first class from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for CGI to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Cape Girardeau Municipal (CGI)?
From Cape Girardeau Municipal (CGI), you can fly into O'Hare Intl. (ORD) to reach Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Cape Girardeau, MO (CGI-Cape Girardeau Municipal) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Cape Girardeau Municipal
Destination airport
Midway Intl.
Distance
329 mi

Book with confidence

Cape Girardeau to Chicago Flights

The cheapest times to fly from Cape Girardeau to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Cape Girardeau to Chicago are during the month of . You can find some of the cheapest flights from Cape Girardeau to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Cape Girardeau to Chicago

Sunday is one of the best days to book for cheap flights from Cape Girardeau to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Cape Girardeau to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Cape Girardeau to Chicago in 2026. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Cape Girardeau to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Cape Girardeau to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Cape Girardeau to Chicago Flights

*Flight schedules are subject to change.

Explore a world of travel with Expedia

*Available to One Key members.