HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$269+ Cheap flights from Casper (CPR) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CPR — CHI
Nov 6 — Nov 131
Thu 11/6
Thu 11/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Casper to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Casper to Chicago

Cheapest flights from Casper to Chicago
Explore the most affordable flight options available from Casper to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 7, 2025.

This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:05 pmCPR - ORD
1 stop4h 54mUnited Airlines
Sun 11/167:10 amORD - CPR
1 stop6h 21mUnited Airlines
Deal found 10/4$269
This United Airlines deal was found by Cheapflights users on 10/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/246:00 pmCPR - ORD
1 stop4h 59mUnited Airlines
Sun 10/267:10 amORD - CPR
1 stop6h 21mUnited Airlines
Deal found 10/4$320
This United Airlines deal was found by Cheapflights users on 10/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/203:12 pmCPR - ORD
1 stop7h 47mUnited Airlines
Fri 10/248:30 pmORD - CPR
2 stops17h 11mUnited Airlines
Deal found 10/5$438
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/263:18 pmCPR - ORD
1 stop7h 41mUnited Airlines
Mon 12/12:40 pmORD - CPR
1 stop8h 18mUnited Airlines
Deal found 10/6$579
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/256:05 pmCPR - ORD
1 stop4h 54mUnited Airlines
Sat 11/298:47 amORD - CPR
1 stop9h 06mUnited Airlines
Deal found 10/6$706
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/263:18 pmCPR - ORD
1 stop7h 41mUnited Airlines
Sun 11/307:10 amORD - CPR
1 stop8h 31mUnited Airlines
Deal found 10/6$729

Cheap flight deals from Casper to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Casper (CPR) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 7, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(United Airlines)
Provider with most accurate pricing for Casper Natrona County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Casper Natrona County-Chicago (CHI) flights.
Search Deals
From Casper Natrona County to Chicago (CHI)
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Casper to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 7, 2025.
Use the filters below to find and compare flights from Casper to Chicago that are best for you.

Fly from

Casper

Fly to

Chicago

Route

Depart

Return

Price

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Fri 11/14

6:05 pm-11:59 pm

1 stop4h 54m

Chicago O'Hare Intl

Sun 11/16

7:10 am-12:31 pm

1 stop6h 21m

$269

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Sat 2/28

1:25 pm-11:59 pm

1 stop9h 34m

Chicago O'Hare Intl

Tue 3/3

4:05 pm-8:35 pm

1 stop5h 30m

$318

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Fri 10/24

6:00 pm-11:59 pm

1 stop4h 59m

Chicago O'Hare Intl

Sun 10/26

7:10 am-12:31 pm

1 stop6h 21m

$320

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Mon 10/20

3:12 pm-11:59 pm

1 stop7h 47m

Chicago O'Hare Intl

Fri 10/24

8:30 pm-12:41 pm

2 stops17h 11m

$438

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Wed 11/26

3:18 pm-11:59 pm

1 stop7h 41m

Chicago O'Hare Intl

Mon 12/1

1:00 pm-8:17 pm

1 stop8h 17m

$579

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/4

Compare providers for flights from Casper to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Casper to Chicago in October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Casper-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Casper-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Casper-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Casper-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Casper-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Casper to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Casper with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Casper to Chicago
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated October 7, 2025.
See what other customers who have flown with United Airlines from Casper to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,957 reviews

Boarding

7.7

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,957 reviews
United Airlines
7.4
Good
8,957 reviews

Boarding

7.7

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Casper to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Casper to Chicago?

    Casper Natrona County (CPR) is the airport you will fly out of if you book a flight from Casper to Chicago. You should not have trouble finding flights to Chicago from Natrona County; the airport handles an average of 0 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Casper airport to Chicago. It is only a 8.1 mi journey to Natrona County (CPR) from Casper’s city center.

  • How long is the flight from Casper to Chicago?

    United Airlines can get you from Casper to Chicago in just under 4h 54m. Your travel time can differ by up to . The distance from Casper to Chicago is about 946 mi.

  • Can I find deals for flights from Casper to Chicago that include hotel bookings?

    Yes. In addition to deals on Casper to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Casper to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Casper to Chicago.

  • Can I find deals for business class flights from Casper to Chicago?

    Yes. Cheapflights offers flight deals from Casper to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Casper to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Denver to O'Hare Intl flights
Denver to Midway flights
Denver to St. Louis flights
Salt Lake City to O'Hare Intl flights
Denver to Moline flights
Salt Lake City to Midway flights
Salt Lake City to St. Louis flights
Denver to Peoria flights
Jackson to O'Hare Intl flights
Denver to Bloomington flights
Denver to Evansville flights
Salt Lake City to Peoria flights
Salt Lake City to Moline flights
Denver to Rockford flights
Casper to O'Hare Intl flights
Cody to O'Hare Intl flights
Jackson to Midway flights
Denver to Decatur flights
Laramie to O'Hare Intl flights
Denver to Champaign flights
Salt Lake City to Bloomington flights
Jackson to St. Louis flights
Denver to Springfield flights
Salt Lake City to Decatur flights
Salt Lake City to Springfield flights
Gillette to O'Hare Intl flights
Salt Lake City to Champaign flights
Denver to Dubuque flights
Salt Lake City to Evansville flights
Casper to St. Louis flights
Laramie to Midway flights
Cody to Bloomington flights
Salt Lake City to Burlington flights
Casper to Midway flights
Cody to Springfield flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.