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$382 Cheap Flights from Casper (CPR) to Chicago (ORD)

View $382 flight on Tue, Aug 11, 2026Opens in a new window

Popular airlines from Casper, WY (CPR-Natrona County Intl.) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Casper to Chicago (CPR-ORD)

Prices were available within the past 7 days and start at $382 for one-way flights and $318 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, Oct 6 - Sat, Oct 10
CPR
Casper
ORD
Chicago
$318 Roundtrip, found 1 day ago
$318
Roundtrip
found 1 day ago
Select United flight, departing Tue, Oct 6 from Casper to Chicago, returning Sat, Oct 10, priced at $318 found 1 day ago
United
Thu, Sep 3 - Sat, Sep 5
CPR
Casper
ORD
Chicago
$348 Roundtrip, found 5 days ago
$348
Roundtrip
found 5 days ago
Select United flight, departing Thu, Sep 3 from Casper to Chicago, returning Sat, Sep 5, priced at $348 found 5 days ago
United
Thu, Sep 3 - Sat, Sep 5
CPR
Casper
ORD
Chicago
$349 Roundtrip, found 7 hours ago
$349
Roundtrip
found 7 hours ago
Select United flight, departing Thu, Sep 3 from Casper to Chicago, returning Sat, Sep 5, priced at $349 found 7 hours ago
United
Thu, Sep 3 - Sat, Sep 5
CPR
Casper
ORD
Chicago
$351 Roundtrip, found 2 days ago
$351
Roundtrip
found 2 days ago
Select United flight, departing Thu, Sep 3 from Casper to Chicago, returning Sat, Sep 5, priced at $351 found 2 days ago
United
Fri, Sep 18 - Mon, Sep 21
CPR
Casper
ORD
Chicago
$357 Roundtrip, found 1 day ago
$357
Roundtrip
found 1 day ago
Select United flight, departing Fri, Sep 18 from Casper to Chicago, returning Mon, Sep 21, priced at $357 found 1 day ago
United
Tue, Oct 6 - Sat, Oct 10
CPR
Casper
ORD
Chicago
$363 Roundtrip, found 1 day ago
$363
Roundtrip
found 1 day ago
Select United flight, departing Tue, Oct 6 from Casper to Chicago, returning Sat, Oct 10, priced at $363 found 1 day ago
United
Thu, Sep 3 - Sat, Sep 5
CPR
Casper
ORD
Chicago
$368 Roundtrip, found 5 days ago
$368
Roundtrip
found 5 days ago
Select United flight, departing Thu, Sep 3 from Casper to Chicago, returning Sat, Sep 5, priced at $368 found 5 days ago
United
Thu, Aug 6 - Mon, Aug 10
CPR
Casper
ORD
Chicago
$368 Roundtrip, found 4 days ago
$368
Roundtrip
found 4 days ago
Select United flight, departing Thu, Aug 6 from Casper to Chicago, returning Mon, Aug 10, priced at $368 found 4 days ago
United
Thu, Sep 3 - Sat, Sep 5
CPR
Casper
ORD
Chicago
$374 Roundtrip, found 2 days ago
$374
Roundtrip
found 2 days ago
Select United flight, departing Thu, Sep 3 from Casper to Chicago, returning Sat, Sep 5, priced at $374 found 2 days ago
United
Thu, Sep 3 - Sat, Sep 5
CPR
Casper
ORD
Chicago
$378 Roundtrip, found 5 days ago
$378
Roundtrip
found 5 days ago
Select United flight, departing Thu, Sep 3 from Casper to Chicago, returning Sat, Sep 5, priced at $378 found 5 days ago

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 $997
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $997

What you need to know for your flight from Natrona County Intl. to O'Hare Intl.

Casper (CPR) to Chicago (ORD) at a glance

Travel from Casper (CPR) to Chicago (ORD) on this domestic short-haul route with a full-service carrier. Discover the best airfares for Casper as you plan your trip to explore Chicago's iconic landmarks and vibrant neighborhoods. Check out the key details for flights from Natrona County International Airport to O'Hare International Airport, including options for cheap flights from Casper that suit your schedule and travel needs.

  • Fastest flight duration: around 4 hours in-flight, plus roughly 1 hour layover with one stop
  • Route distance: roughly 900 miles (1,450 km)
  • Flights per week: around 7 departures on average
  • Typical fares (one-way): economy tickets often range from $125–$515, depending on seasonality and how far ahead you book

Flights from Natrona County International Airport (CPR) to O'Hare International Airport (ORD)

Based on recent traveler bookings, here are the top airlines favored for the route from Casper to Chicago, typically offering one-stop service with a popular layover at Denver International Airport (DEN), which lasts about an hour. This allows you to combine factors like price, travel time, and cabin class to create the ideal travel itinerary.

  • United: This comprehensive airline offers a convenient one-stop travel option, dominating departures on this route. One-way ticket prices generally fall between $125 and $515, with an in-flight duration of approximately 4 hours, leading to a total travel time of around 5 hours, including layover time.

Alternative routes from Casper (CPR) to Chicago (ORD)

  • Casper to Chicago (CPR-MDW): Midway International Airport (MDW) is located roughly 16 miles from O'Hare International Airport (ORD).
  • Rawlins to Chicago (RWL-ORD): Rawlins Municipal Airport (RWL) is about 85 miles from Natrona County International Airport (CPR).

How to find the best prices for flights from Casper (CPR) to Chicago (ORD)

Getting some of the best deals on flights from Casper to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually found when booking at least two months in advance, although most travelers tend to book between two to eight weeks ahead. Morning departures from 5 a.m. to 12 p.m. often offer lower prices and are the most popular flight times, while flying on Saturday generally results in cheaper rates, with Thursday being the most favored travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at O'Hare International Airport from Natrona County International Airport

Chicago welcomes travelers from Casper with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from O'Hare International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at O'Hare International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From O'Hare International Airport, O'Hare Station (a metro station) is conveniently located just 0.1 miles away on foot, while Rosemont Station (a train station) is situated about 2.2 miles from the airport, typically reached by car.

Frequently asked questions

How much does a flight from Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from $382 and cheap return flights from $318 Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.) with Expedia. One-way flights usually range from $494 to $972, and return flights typically cost between $411 and $4111. 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 the cheapest fares first, and use the Price Tracking tool to receive alerts when Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest month to fly from CPR to ORD is October 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 Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter CPR to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
United is one of the cheapest airlines offering connecting flights from Natrona County Intl. (CPR) to O'Hare Intl. (ORD), with round-trip tickets starting from around $248 with a layover in Denver Intl. (DEN). Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare 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 Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare 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 Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from Casper, Wyoming (CPR) to Chicago, Illinois (ORD) usually leaves at around 5:15 AM, with United Airlines providing the service. This seasonal option allows you to make the most of your day in Chicago. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from Casper, WY (CPR) to Chicago, IL (ORD) are in the late morning, from 9am to noon. About 31% of passengers prefer this time window. Many major carriers, including United Airlines, offer flights during this window. This timing works well because it allows you to travel after the morning rush and arrive in Chicago with plenty of time to enjoy the city.
How long does it take to fly from Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Flying from CPR to ORD with a connection usually takes about 5 hours, traveling roughly 947 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
First class seats are offered on the CPR to ORD route with United Airlines.
How do I earn miles on a Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare 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 Natrona County Intl. (CPR)?
If you're planning to travel to Chicago from Natrona County Intl. (CPR), you can fly into O'Hare Intl. (ORD) Some flights may connect through major hubs like Denver Intl. (DEN) before reaching 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 Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare 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 Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare 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 Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your Casper, WY (CPR-Natrona County Intl.) to Chicago, IL (ORD-O'Hare 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
Natrona County Intl.
Destination airport
O'Hare Intl.
Airlines serving
United
Roundtrip price
$318
Distance
946 mi

Book with confidence

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 2026. You can also book with separate airlines for your outbound and return journeys, from $382 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.

 

Casper to Chicago Flights

*Flight schedules are subject to change.

*Available to One Key members.

 

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