$448+ Cheap flights from Chicago (CHI) to Cheyenne (CYS)
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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — CYS
Nov 1 — Nov 81
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Cheyenne 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.Cheap flight deals from Chicago to Cheyenne
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Best
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Cheapest flights from Chicago to CheyenneExplore the most affordable flight options available from Chicago to Cheyenne. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2026.
Explore the most affordable flight options available from Chicago to Cheyenne. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 2, 2026.
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Sat 10/35:51 pm -
1 stop5h 07m
Mon 10/51:40 pm -
1 stop7h 12m
Deal found 9/29![United Airlines logo]()
$448
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Wed 12/97:00 am -
1 stop7h 16m
Mon 12/141:54 pm -
1 stop4h 34m
Deal found 10/1![United Airlines logo]()
$450
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/133:50 pm -
1 stop7h 08m
Sat 10/171:40 pm -
1 stop5h 40m
Deal found 9/28![United Airlines logo]()
$458
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/157:00 am -
1 stop7h 04m
Mon 10/191:40 pm -
1 stop7h 12m
Deal found 9/30![United Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 10/141:30 pm -
1 stop9h 28m
Sun 10/181:40 pm -
1 stop8h 06m
Deal found 9/29![United Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/26:00 am -
1 stop8h 04m
Mon 10/51:40 pm -
1 stop7h 12m
Deal found 9/30![United Airlines logo]()
$609
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/167:00 am -
1 stop7h 04m
Tue 10/201:40 pm -
1 stop4h 50m
Deal found 10/1![United Airlines logo]()
$678
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/45:00 am -
1 stop9h 04m
Tue 10/66:00 am -
1 stop4h 28m
Deal found 9/30![United Airlines logo]()
$710
Best flights from Chicago to CheyenneDiscover carefully curated flight deals from Chicago to Cheyenne that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 2, 2026.
Discover carefully curated flight deals from Chicago to Cheyenne that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 2, 2026.
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Wed 12/97:00 am -
1 stop7h 16m
Mon 12/141:54 pm -
1 stop4h 34m
Deal found 10/1![United Airlines logo]()
$450
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/133:50 pm -
1 stop7h 08m
Sat 10/171:40 pm -
1 stop5h 40m
Deal found 9/28![United Airlines logo]()
$458
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/157:00 am -
1 stop7h 04m
Mon 10/191:40 pm -
1 stop7h 12m
Deal found 9/30![United Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 10/2. 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.
Sat 10/177:00 am -
1 stop7h 04m
Wed 10/211:40 pm -
1 stop4h 50m
Deal found 10/2![United Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/167:00 am -
1 stop7h 04m
Tue 10/201:40 pm -
1 stop4h 50m
Deal found 10/1![United Airlines logo]()
$678
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 10/144:00 pm -
2 stops6h 58m
Sun 10/181:40 pm -
1 stop9h 19m
Deal found 9/29![United Airlines logo]()
$730
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/124:00 pm -
2 stops22h 04m
Fri 10/161:40 pm -
1 stop6h 38m
Deal found 9/28![United Airlines logo]()
$738
Last-minute flights from Chicago to CheyenneDiscover last-minute flight deals from Chicago to Cheyenne. Data last updated October 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Cheyenne. Data last updated October 2, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/26:00 am -
1 stop8h 04m
Mon 10/51:40 pm -
1 stop7h 12m
Deal found 9/30![United Airlines logo]()
$609
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Sat 10/35:51 pm -
1 stop5h 07m
Mon 10/51:40 pm -
1 stop7h 12m
Deal found 9/29![United Airlines logo]()
$448
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/45:00 am -
1 stop9h 04m
Tue 10/66:00 am -
1 stop4h 28m
Deal found 9/30![United Airlines logo]()
$710
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/124:00 pm -
2 stops22h 04m
Fri 10/161:40 pm -
1 stop6h 38m
Deal found 9/28![United Airlines logo]()
$738
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/133:50 pm -
1 stop7h 08m
Sat 10/171:40 pm -
1 stop5h 40m
Deal found 9/28![United Airlines logo]()
$458
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 10/141:30 pm -
1 stop9h 28m
Sun 10/181:40 pm -
1 stop8h 06m
Deal found 9/29![United Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 9/30. 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 10/157:00 am -
1 stop7h 04m
Mon 10/191:40 pm -
1 stop7h 12m
Deal found 9/30![United Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 10/1. 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 10/167:00 am -
1 stop7h 04m
Tue 10/201:40 pm -
1 stop4h 50m
Deal found 10/1![United Airlines logo]()
$678
Find flight deals from Chicago to Cheyenne
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Cheyenne (CYS). 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 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $450 (United Airlines) |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Cheyenne 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 7,457,451 searches. Data last updated October 2, 2026.
Use the filters below to find and compare flights from Chicago to Cheyenne that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoCheyenne
ORD Chicago O'Hare Intl - CYS Cheyenne
ORDCYS
Chicago O'Hare Intl
Wed 12/9
7:00 am-1:16 pm
1 stop7h 16m
Cheyenne
Mon 12/14
1:54 pm-7:28 pm
1 stop4h 34m
$450
ChicagoCheyenne
ORD Chicago O'Hare Intl - CYS Cheyenne
ORDCYS
Chicago O'Hare Intl
Tue 10/13
3:50 pm-9:58 pm
1 stop7h 08m
Cheyenne
Sat 10/17
1:40 pm-8:20 pm
1 stop5h 40m
$458
ChicagoCheyenne
ORD Chicago O'Hare Intl - CYS Cheyenne
ORDCYS
Chicago O'Hare Intl
Thu 10/15
7:00 am-1:04 pm
1 stop7h 04m
Cheyenne
Mon 10/19
1:40 pm-9:52 pm
1 stop7h 12m
$484
ChicagoCheyenne
ORD Chicago O'Hare Intl - CYS Cheyenne
ORDCYS
Chicago O'Hare Intl
Sat 10/17
7:00 am-1:04 pm
1 stop7h 04m
Cheyenne
Wed 10/21
1:40 pm-7:30 pm
1 stop4h 50m
$564
ChicagoCheyenne
ORD Chicago O'Hare Intl - CYS Cheyenne
ORDCYS
Chicago O'Hare Intl
Fri 10/16
7:00 am-1:04 pm
1 stop7h 04m
Cheyenne
Tue 10/20
1:40 pm-7:30 pm
1 stop4h 50m
$678
ChicagoCheyenne
ORD Chicago O'Hare Intl - CYS Cheyenne
ORDCYS
Chicago O'Hare Intl
Wed 10/14
4:00 pm-9:58 pm
2 stops6h 58m
Cheyenne
Sun 10/18
1:40 pm-11:59 pm
1 stop9h 19m
$730
ChicagoCheyenne
ORD Chicago O'Hare Intl - CYS Cheyenne
ORDCYS
Chicago O'Hare Intl
Mon 10/12
4:00 pm-1:04 pm
2 stops22h 04m
Cheyenne
Fri 10/16
1:40 pm-9:18 pm
1 stop6h 38m
$738
Sorted by cheapest first
Compare providers for flights from Chicago to Cheyenne
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 Chicago to Cheyenne in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Cheyenne flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Cheyenne flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Cheyenne flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Cheyenne 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 Chicago-Cheyenne 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 Chicago to Cheyenne
Have a flexible travel schedule? Discover the best time to fly to Cheyenne from Chicago with our price prediction graph.
CHI-CYS
ORD-CYS
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 Chicago to Cheyenne
CHI-CYS
ORD-CYS
No data available for this route at this time. Please check back soon.
Related info for your journey
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