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$308+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
CPR — CHI
Jul 3 — Jul 101
Fri 7/3
Fri 7/10
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 June 3, 2026.

This United Airlines deal was found by Cheapflights users on 6/2. 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 7/16:05 pm
CPR
-
ORD
1 stop5h 39m
United Airlines
Wed 7/85:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 6/2$308
This United Airlines deal was found by Cheapflights users on 5/31. 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
Tue 7/215:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 5/31$341
This United Airlines deal was found by Cheapflights users on 6/3. 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 9/171:26 pm
CPR
-
ORD
1 stop8h 20m
United Airlines
Mon 9/215:00 am
ORD
-
CPR
1 stop4h 50m
United Airlines
Deal found 6/3$388
This United Airlines deal was found by Cheapflights users on 6/1. 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 7/36:13 pm
CPR
-
ORD
1 stop5h 31m
United Airlines
Mon 7/65:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 6/1$442
This United Airlines deal was found by Cheapflights users on 5/29. 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 6/2311:21 am
CPR
-
ORD
1 stop9h 33m
United Airlines
Fri 6/2610:00 pm
ORD
-
CPR
2 stops20h 29m
United Airlines
Deal found 5/29$528
This United Airlines deal was found by Cheapflights users on 6/1. 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 6/43:15 pm
CPR
-
ORD
1 stop6h 34m
United Airlines
Mon 6/85:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 6/1$530
This United Airlines deal was found by Cheapflights users on 6/3. 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 6/186:13 pm
CPR
-
ORD
1 stop5h 31m
United Airlines
Mon 6/225:00 am
ORD
-
CPR
1 stop4h 51m
United Airlines
Deal found 6/3$614

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 June 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip 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

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 June 3, 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

Wed 7/1

6:05 pm-12:44 am

1 stop5h 39m

Chicago O'Hare Intl

Wed 7/8

5:00 am-8:51 am

1 stop4h 51m

$308

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Thu 9/17

1:26 pm-11:59 pm

1 stop9h 33m

Chicago O'Hare Intl

Mon 9/21

2:32 pm-9:59 pm

1 stop8h 27m

$388
Quickest round-trip

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Fri 7/3

6:13 pm-12:44 am

1 stop5h 31m

Chicago O'Hare Intl

Mon 7/6

5:00 am-8:51 am

1 stop4h 51m

$442

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Fri 7/17

6:13 pm-12:44 am

1 stop5h 31m

Chicago O'Hare Intl

Tue 7/21

9:25 pm-10:46 am

2 stops14h 21m

$507

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Tue 6/23

11:21 am-9:54 pm

1 stop9h 33m

Chicago O'Hare Intl

Fri 6/26

10:00 pm-5:29 pm

2 stops20h 29m

$528

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Thu 6/18

6:13 pm-12:44 am

1 stop5h 31m

Chicago O'Hare Intl

Mon 6/22

5:00 am-8:51 am

1 stop4h 51m

$614

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Thu 7/30

5:15 am-1:00 pm

2 stops6h 45m

Chicago O'Hare Intl

Sat 8/1

5:00 am-8:51 am

1 stop4h 51m

$661
Cheapest one-way
Quickest one-way

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Mon 7/20

6:13 pm-7:30 am

2 stops12h 17m

$407

CasperChicago

CPR - ORD

CPRORD

Casper Natrona County

Sun 7/19

6:13 pm-10:02 am

2 stops14h 49m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/30

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

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 39m. 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?

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