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$308+ Cheap flights from Casper (CPR) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
CPR — CHI
May 19 — May 261
Tue 5/19
Tue 5/26
1 adult, Economy
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Cheap 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 April 19, 2026.

This United Airlines deal was found by Cheapflights users on 4/15. 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 7/176:13 pm
CPR
-
ORD
1 stop5h 31m
United Airlines
Fri 7/245:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 4/15$328
This United Airlines deal was found by Cheapflights users on 4/16. 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 5/16:10 pm
CPR
-
ORD
1 stop4h 47m
United Airlines
Tue 5/53:00 pm
ORD
-
CPR
1 stop4h 57m
United Airlines
Deal found 4/16$358
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Thu 4/306:10 pm
CPR
-
ORD
1 stop5h 48m
United Airlines
Mon 5/43:00 pm
ORD
-
CPR
1 stop4h 57m
United Airlines
Deal found 4/15$385
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Sat 6/2011:15 am
CPR
-
ORD
1 stop9h 24m
United Airlines
Fri 6/265:00 am
ORD
-
CPR
1 stop6h 46m
United Airlines
Deal found 4/16$408
This United Airlines deal was found by Cheapflights users on 4/15. 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.
Thu 5/216:13 pm
CPR
-
ORD
1 stop5h 31m
United Airlines
Sat 5/235:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 4/15$428
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Thu 5/216:13 pm
CPR
-
ORD
1 stop5h 31m
United Airlines
Mon 5/256:00 am
ORD
-
CPR
1 stop5h 46m
United Airlines
Deal found 4/17$478
This United Airlines deal was found by Cheapflights users on 4/16. 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 6/221:23 pm
CPR
-
ORD
1 stop6h 21m
United Airlines
Sat 6/275:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 4/16$534
This United Airlines deal was found by Cheapflights users on 4/16. 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 6/223:15 pm
CPR
-
ORD
2 stops17h 02m
United Airlines
Sun 6/285:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 4/16$542
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Sun 6/2111:21 am
CPR
-
ORD
1 stop8h 23m
United Airlines
Sun 6/285:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 4/16$552
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Sat 6/2011:15 am
CPR
-
ORD
1 stop7h 50m
United Airlines
Sun 6/288:09 pm
ORD
-
CPR
2 stops13h 42m
United Airlines
Deal found 4/16$582

Find 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 April 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$328
(United Airlines)

One-way from

$308
(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
One-way flight 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 April 19, 2026.
Use the filters below to find and compare flights from Casper to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Thu 4/30

6:10 pm-12:58 am

1 stop5h 48m

Chicago O'Hare Intl

Mon 5/4

3:00 pm-6:57 pm

1 stop4h 57m

$385

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Thu 5/21

6:13 pm-12:44 am

1 stop5h 31m

Chicago O'Hare Intl

Mon 5/25

5:00 am-8:51 am

1 stop4h 51m

$408

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Thu 5/21

6:13 pm-12:44 am

1 stop5h 31m

Chicago O'Hare Intl

Sat 5/23

5:00 am-8:51 am

1 stop4h 51m

$428

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Mon 6/22

1:23 pm-8:44 pm

1 stop6h 21m

Chicago O'Hare Intl

Sat 6/27

5:00 am-8:51 am

1 stop4h 51m

$534

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Tue 6/23

3:15 pm-9:17 am

2 stops17h 02m

Chicago O'Hare Intl

Sat 6/27

5:00 am-8:51 am

1 stop4h 51m

$627

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Fri 7/17

5:15 am-12:40 pm

2 stops6h 25m

Chicago O'Hare Intl

Fri 7/24

5:00 am-8:51 am

1 stop4h 51m

$696
Quickest round-trip

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Sun 5/3

6:10 pm-11:57 pm

1 stop4h 47m

Chicago O'Hare Intl

Thu 5/7

4:10 pm-8:17 pm

1 stop5h 07m

$746

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Fri 5/1

11:23 am-6:54 pm

2 stops6h 31m

Chicago O'Hare Intl

Tue 5/5

7:00 am-10:48 am

1 stop4h 48m

$775
Cheapest one-way

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Thu 6/25

6:13 pm-12:44 am

1 stop5h 31m

$308
Quickest one-way

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Fri 5/1

3:14 pm-9:23 pm

1 stop5h 09m

$373

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Sorted by cheapest first

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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.

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 5h 31m. 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
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Merrillville
Hammond
Porter

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