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$68+ Cheap flights from Chicago (CHI) to Wyoming

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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAC
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Find flight deals from Chicago to Wyoming

Cheapest flights from Chicago to Wyoming
Explore the most affordable flight options available from Chicago to Wyoming. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:00 amORD - DEN
Nonstop2h 41mFrontier
Mon 11/178:44 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 10/19$93
This Priceline deal was found by Cheapflights users on 10/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1312:30 pmMDW - DEN
Nonstop2h 46mFrontier
Mon 11/178:05 amDEN - MDW
Nonstop2h 25mFrontier
Deal found 10/19$93
This Cheapflightsfares deal was found by Cheapflights users on 10/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/146:00 amORD - DEN
Nonstop2h 41mFrontier
Mon 11/178:44 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 10/19$94
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:28 amORD - DEN
1 stop8h 25mMultiple Airlines
Tue 11/184:00 pmDEN - ORD
Nonstop2h 38mMultiple Airlines
Deal found 10/19$95
This Priceline deal was found by Cheapflights users on 10/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:05 pmORD - DEN
Nonstop2h 54mFrontier
Sun 11/168:44 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 10/19$97
This Priceline deal was found by Cheapflights users on 10/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/263:31 pmMDW - DEN
Nonstop2h 51mFrontier
Sun 12/77:45 amDEN - MDW
Nonstop2h 23mFrontier
Deal found 10/19$97
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:05 pmORD - DEN
Nonstop2h 54mFrontier
Sat 11/1512:25 pmDEN - ORD
1 stop10h 04mFrontier
Deal found 10/20$99
This Frontier deal was found by Cheapflights users on 10/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/811:36 amMDW - DEN
1 stop7h 39mFrontier
Sun 11/98:05 amDEN - MDW
Nonstop2h 25mFrontier
Deal found 10/18$99
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:15 amORD - DEN
Nonstop2h 49mFrontier
Wed 11/1911:26 amDEN - ORD
1 stop12h 33mFrontier
Deal found 10/20$100
This Mytrip deal was found by Cheapflights users on 10/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:15 amORD - DEN
Nonstop2h 49mFrontier
Mon 11/177:08 amDEN - ORD
1 stop15h 36mFrontier
Deal found 10/20$101
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amORD - DEN
Nonstop2h 41mFrontier
Mon 11/38:44 pmDEN - ORD
Nonstop2h 31mFrontier
Deal found 10/20$102
This Priceline deal was found by Cheapflights users on 10/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:30 pmMDW - DEN
Nonstop2h 46mFrontier
Sun 11/28:05 amDEN - MDW
Nonstop2h 25mFrontier
Deal found 10/19$102

Cheap flight deals from Chicago to Wyoming

Keep the following information in mind while searching for Chicago to Wyoming flight deals. Data was last updated October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$93
(Cheapflightsfares)

One-way from

$68
(Kiwi.com)

Popular in

February

Cheapest in

October

Average price

$379

Good round-trip deal

$379 or less

Good one-way deal

$210 or less
Provider with most accurate pricing for Chicago (CHI)-Jackson Hole flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Jackson Hole flights.
Search Deals
From Chicago (CHI) to Wyoming
Search Deals
One-way flight from Chicago (CHI) to Wyoming
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Wyoming.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Wyoming.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Wyoming 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 20, 2025.
Use the filters below to find and compare flights from Chicago to Wyoming that are best for you.

Fly from

Chicago

Fly to

Wyoming

Route

Depart

Return

Price

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sun 1/18

1:15 pm-4:20 pm

1 stop4h 05m

Denver Intl

Sun 2/1

5:25 am-8:55 am

Nonstop2h 30m

$160

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Wed 12/10

2:35 pm-4:15 pm

Nonstop2h 40m

Denver Intl

Sun 12/14

7:35 pm-10:55 pm

Nonstop2h 20m

$173

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 12/4

7:05 am-8:45 am

Nonstop2h 40m

Denver Intl

Sun 12/7

7:35 pm-10:55 pm

Nonstop2h 20m

$182

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 1/1

7:05 am-8:45 am

Nonstop2h 40m

Denver Intl

Tue 1/6

8:45 am-2:55 pm

1 stop5h 10m

$184

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Fri 1/2

9:40 pm-11:38 pm

Nonstop2h 58m

Denver Intl

Tue 1/6

7:50 am-11:34 am

Nonstop2h 44m

$190

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sun 12/21

5:50 pm-9:50 pm

1 stop5h 00m

Denver Intl

Tue 12/30

1:10 pm-5:40 pm

1 stop3h 30m

$192

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 12/10

8:55 am-2:12 pm

1 stop6h 17m

Denver Intl

Fri 12/12

12:50 am-8:39 am

1 stop6h 49m

$197

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Tue 11/18

6:00 am-12:43 pm

1 stop7h 43m

Denver Intl

Wed 11/19

10:39 am-7:23 pm

1 stop7h 44m

$197

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Wed 1/14

1:00 pm-5:37 pm

1 stop5h 37m

Denver Intl

Tue 1/20

11:10 am-6:08 pm

1 stop5h 58m

$197

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 12/6

5:15 pm-6:55 pm

Nonstop2h 40m

Denver Intl

Sun 12/7

7:40 am-11:05 am

Nonstop2h 25m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Wyoming

Have a flexible travel schedule? Discover the best time to fly to Wyoming from Chicago 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 Chicago to Wyoming

What is the cheapest month to book a flight from Chicago to Wyoming?

Currently, October is the cheapest month in which you can book a flight from Chicago to Wyoming (average of $229). Flying from Chicago to Wyoming in February is currently the most expensive (average of $383). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to WY?

Find hourly flight availability from Chicago to Wyoming. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 20, 2025.

When flying from Chicago to Wyoming, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 12% versus a flight in the morning.

Weekly flight availability from Chicago to Wyoming

Explore weekly flight availability from Chicago to Wyoming. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 20, 2025.

The most flights from CHI to USWY are scheduled on a Monday (2 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Chicago to Wyoming?

Reviews of airlines servicing Wyoming

Get insights into the airlines that provide service to Wyoming. 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 Wyoming. Reviews last updated October 20, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Chicago to Wyoming by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,978 reviews
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,991 reviews
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,024 reviews
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

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

  • How long is the flight from Chicago to Wyoming?

    There are many flights that can get you from Chicago to Wyoming in 2h 58m. Fly via Southwest, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 886 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Wyoming one-way?

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $68. However, be on the lookout for offers from United Airlines and Alaska Airlines, as they are both options that can get you from Chicago to Wyoming for a low price.

  • What are the most popular routes from Chicago to Wyoming?

    The most popular flight routes from Chicago to Wyoming are Chicago O'Hare Intl - Denver Intl, Chicago O'Hare Intl - Salt Lake City and Chicago Midway - Denver Intl.

  • What are the most reliable airlines from Chicago to Wyoming?

    The top 3 most reliable airlines when flying from Chicago to Wyoming are American Airlines (76%), Copa Airlines (64%) and United Airlines (61%).

  • What are the cheapest flights from Chicago to Wyoming?

    While on average a flight from Chicago to Wyoming is generally $362, our data shows the cheapest flight currently is $210. When looking at the most popular route, (Chicago O'Hare Intl - Denver Intl), you can expect to pay $78 for that flight.

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

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

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

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

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

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

  • What is the cheapest month to book a flight from Chicago to Wyoming?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Wyoming (average of $229). Flying from Chicago to Wyoming in February is currently the most expensive (average of $383). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Chicago to Wyoming

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Wyoming

Discover the top 3 airlines that operate flights from Chicago to Wyoming. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$211Average$447FlexibilityNo cancel feeOn-time69%
DeltaCheapest$265Average$413FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$287Average$477FlexibilityNo cancel feeOn-time71%

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