$613 Cheap Flights from Casper (CPR) to Chicago (MDW)

View $613 flight on Tue, Sep 23, 2025Opens in a new window

Popular airlines from Casper, WY (CPR-Natrona County Intl.) to Chicago Midway Airport (MDW)

Cheap Flights from Casper to Chicago (CPR-MDW)

Prices were available within the past 7 days and start at $613 for one-way flights and $1,225 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, Oct 21 - Sat, Oct 25
CPR
Casper
MDW
Chicago
$1,225 Roundtrip, found 3 days ago
$1,225
Roundtrip
found 3 days ago
Select United flight, departing Tue, Oct 21 from Casper to Chicago, returning Sat, Oct 25, priced at $1,225 found 3 days ago
United
Tue, Aug 12 - Sat, Aug 16
CPR
Casper
MDW
Chicago
$1,226 Roundtrip, found 1 day ago
$1,226
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 12 from Casper to Chicago, returning Sat, Aug 16, priced at $1,226 found 1 day ago
United
Wed, Aug 13 - Tue, Aug 26
CPR
Casper
MDW
Chicago
$1,231 Roundtrip, found 1 day ago
$1,231
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 13 from Casper to Chicago, returning Tue, Aug 26, priced at $1,231 found 1 day ago
United
Wed, Aug 13 - Sat, Aug 16
CPR
Casper
MDW
Chicago
$1,231 Roundtrip, found 1 day ago
$1,231
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 13 from Casper to Chicago, returning Sat, Aug 16, priced at $1,231 found 1 day ago
United
Thu, Oct 23 - Sun, Oct 26
CPR
Casper
MDW
Chicago
$1,237 Roundtrip, found 3 days ago
$1,237
Roundtrip
found 3 days ago
Select United flight, departing Thu, Oct 23 from Casper to Chicago, returning Sun, Oct 26, priced at $1,237 found 3 days ago
United
Sat, Aug 9 - Tue, Aug 26
CPR
Casper
MDW
Chicago
$1,241 Roundtrip, found 1 day ago
$1,241
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 9 from Casper to Chicago, returning Tue, Aug 26, priced at $1,241 found 1 day ago
United
Sat, Aug 9 - Tue, Aug 12
CPR
Casper
MDW
Chicago
$1,241 Roundtrip, found 1 day ago
$1,241
Roundtrip
found 1 day ago
Select United flight, departing Sat, Aug 9 from Casper to Chicago, returning Tue, Aug 12, priced at $1,241 found 1 day ago
United
Tue, Aug 12 - Wed, Aug 20
CPR
Casper
MDW
Chicago
$1,248 Roundtrip, found 1 day ago
$1,248
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 12 from Casper to Chicago, returning Wed, Aug 20, priced at $1,248 found 1 day ago
United
Thu, Oct 23 - Sun, Oct 26
CPR
Casper
MDW
Chicago
$1,249 Roundtrip, found 3 days ago
$1,249
Roundtrip
found 3 days ago
Select United flight, departing Thu, Oct 23 from Casper to Chicago, returning Sun, Oct 26, priced at $1,249 found 3 days ago
United
Wed, Aug 13 - Wed, Aug 20
CPR
Casper
MDW
Chicago
$1,253 Roundtrip, found 1 day ago
$1,253
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 13 from Casper to Chicago, returning Wed, Aug 20, priced at $1,253 found 1 day ago
Flights from Casper (CPR) to Chicago (MDW)
Origin airport
Natrona County Intl.
Destination airport
Midway Intl.
Roundtrip price
$1,225
Distance
957 mi

Casper to Chicago Flights

The cheapest times to fly from Casper 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 Casper to Chicago are during the month of October. You can find some of the cheapest flights from Casper to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Casper to Chicago

Sunday is one of the best days to book for cheap flights from Casper 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 Casper 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 Casper to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $613 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 Casper 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 Casper 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.

 

Frequently asked questions

How much does a flight from Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $613 or cheap return flight from $1,225 from Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW)?
October is the least expensive month to fly from CPR to MDW. Traveling during quieter months is often the key to finding better fares.
What is the cheapest airline that flies from Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll fly you from CPR to MDW. Then, sort your results by "Price (lowest to highest)" to snag the best deal available.
How many flights per day from Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW)?
Nonstop flights from Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW) aren't available daily, so you'll need to take a flight with a layover. Explore your options with Expedia's filters. Enter your dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from CPR to MDW?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on a number of factors, including the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later flights are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from CPR to MDW are usually more expensive. For the best prices, start searching for flights well in advance. That being said, if you can play around with your travel dates, it's possible to find a cheap fare just before your departure.
Is it cheaper to book a CPR to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a CPR to MDW flight and hotel package with Expedia could result in significant savings. What's more, having everything in one place will take the hassle out of travel planning. Simply pick your flights and choose from our wide range of stays, then tailor your trip with extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Natrona County Intl. Airport (CPR) to Midway Intl. Airport (MDW)?
If you reserved your CPR to MDW flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.

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*Available to One Key members.