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$79+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JAC
Feb 15 — Feb 221
Sun 2/15
Sun 2/22
1 adult, Economy
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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 January 16, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$114
(Kiwi.com)

One-way from

$79
(Kiwi.com)

Popular in

November

Cheapest in

October

Average price

$516

Good round-trip deal

$354 or less

Good one-way deal

$153 or less
Provider with most accurate pricing for Chicago (CHI)-Jackson Hole flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Jackson Hole flights.
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From Chicago (CHI) to Wyoming
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One-way flight from Chicago (CHI) to Wyoming
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Highest demand for flights based on searches. 5% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Chicago (CHI) to Wyoming.
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Price to beat on a one-way flight from Chicago (CHI) to Wyoming.
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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 January 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/13. 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.
Thu 2/264:16 pm
ORD
-
DEN
Nonstop3h 07m
Frontier
Mon 3/26:00 am
DEN
-
ORD
1 stop7h 30m
Frontier
Deal found 1/13$114
This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Fri 3/66:30 pm
ORD
-
DEN
Nonstop3h 04m
Frontier
Tue 3/108:17 am
DEN
-
ORD
1 stop5h 58m
Frontier
Deal found 1/14$115
This Cheapflightsfares deal was found by Cheapflights users on 1/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:30 pm
ORD
-
DEN
Nonstop3h 04m
Frontier
Fri 3/209:29 pm
DEN
-
ORD
Nonstop2h 38m
Frontier
Deal found 1/15$116
This Frontier deal was found by Cheapflights users on 1/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/166:30 pm
ORD
-
DEN
Nonstop3h 04m
Frontier
Thu 3/196:00 am
DEN
-
ORD
Nonstop2h 43m
Frontier
Deal found 1/15$117
This Frontier deal was found by Cheapflights users on 1/14. 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.
Thu 2/55:40 am
ORD
-
DEN
1 stop7h 39m
Frontier
Thu 2/52:57 pm
DEN
-
ORD
Nonstop2h 34m
Frontier
Deal found 1/14$118
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/14:16 pm
ORD
-
DEN
Nonstop3h 07m
Frontier
Mon 3/212:59 am
DEN
-
ORD
1 stop8h 52m
Frontier
Deal found 1/15$119
This Kiwi.com deal was found by Cheapflights users on 1/14. 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 4/45:52 pm
ORD
-
DEN
Nonstop3h 08m
Frontier
Tue 4/711:59 pm
DEN
-
ORD
1 stop8h 03m
Frontier
Deal found 1/14$120
This Orbitz deal was found by Cheapflights users on 1/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:30 am
ORD
-
DEN
1 stop12h 40m
Frontier
Sat 4/119:00 pm
DEN
-
ORD
Nonstop2h 38m
Frontier
Deal found 1/14$121
This Cheapflightsfares deal was found by Cheapflights users on 1/14. 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 2/194:16 pm
ORD
-
DEN
Nonstop3h 07m
Frontier
Mon 2/235:01 am
DEN
-
ORD
1 stop17h 14m
Frontier
Deal found 1/14$122
This Frontier deal was found by Cheapflights users on 1/14. 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.
Thu 2/194:16 pm
ORD
-
DEN
Nonstop3h 07m
Frontier
Mon 2/2312:59 am
DEN
-
ORD
1 stop8h 52m
Frontier
Deal found 1/14$123
This Frontier deal was found by Cheapflights users on 1/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:51 am
ORD
-
DEN
1 stop10h 44m
Frontier
Fri 2/208:24 am
DEN
-
ORD
Nonstop2h 34m
Frontier
Deal found 1/15$124
This Priceline deal was found by Cheapflights users on 1/14. 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 4/32:29 pm
ORD
-
DEN
Nonstop3h 20m
Frontier
Mon 4/69:45 am
DEN
-
ORD
Nonstop2h 34m
Frontier
Deal found 1/14$125

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 January 16, 2026.
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

Wed 2/11

2:10 pm-3:50 pm

Nonstop2h 40m

Denver Intl

Wed 2/18

6:25 pm-9:50 pm

Nonstop2h 25m

$179

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Wed 2/11

10:05 am-11:50 am

Nonstop2h 45m

Denver Intl

Sat 2/14

7:20 am-10:55 am

Nonstop2h 35m

$187

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Wed 3/4

2:40 pm-4:36 pm

Nonstop2h 56m

Denver Intl

Sun 3/8

6:00 am-9:38 am

Nonstop2h 38m

$188

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 2/17

8:00 am-9:50 am

Nonstop2h 50m

Denver Intl

Wed 2/18

10:15 am-4:25 pm

1 stop5h 10m

$189

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sun 2/22

9:04 pm-7:39 am

1 stop11h 35m

Denver Intl

Sat 2/28

7:00 am-3:19 pm

1 stop7h 19m

$195

ChicagoDenver

ORD - DEN

ORDDEN

Chicago O'Hare Intl

Sat 4/25

2:05 pm-7:05 pm

1 stop6h 00m

Denver Intl

Tue 4/28

11:25 am-3:00 pm

Nonstop2h 35m

$195

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sun 2/22

9:35 pm-11:15 pm

Nonstop2h 40m

Denver Intl

Sat 2/28

7:20 am-10:55 am

Nonstop2h 35m

$196

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Sat 2/14

8:45 pm-10:30 pm

Nonstop2h 45m

Denver Intl

Sat 2/21

8:00 am-1:20 pm

1 stop4h 20m

$197

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Tue 2/10

8:15 am-12:05 pm

1 stop4h 50m

Denver Intl

Wed 2/11

7:00 am-2:20 pm

1 stop6h 20m

$199

ChicagoDenver

MDW - DEN

MDWDEN

Chicago Midway

Thu 4/30

5:30 am-10:15 am

1 stop5h 45m

Denver Intl

Thu 5/7

6:35 am-9:55 am

Nonstop2h 20m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

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 November is currently the most expensive (average of $355). 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 January 16, 2026.

When flying from Chicago to Wyoming, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 January 16, 2026.

The most flights from CHI to USWY are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, 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 January 16, 2026.
Get a feel of what it's like to fly with 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.
United Airlines
7.4
Good
9,163 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,163 reviews
United Airlines
7.4
Good
9,163 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.2
Good
11,136 reviews
United Airlines
7.4
Good
9,163 reviews

Comfort

7.3

Boarding

7.7

Food

6.6

Crew

8.1

Overall

7.4

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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 40m. Fly via Southwest, United Airlines, or Frontier to get the fastest option. Airlines will cover a distance of 893 mi. This flight may include one or multiple stops.

  • 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 cheapest flights from Chicago to Wyoming?

    While on average a flight from Chicago to Wyoming is generally $312, our data shows the cheapest flight currently is $153. When looking at the most popular route, (Chicago O'Hare Intl - Denver Intl), you can expect to pay $82 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 November is currently the most expensive (average of $355). 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.
O'Hare Intl to Sky Harbor Intl flights
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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 January 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$211Average$457FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$274Average$469FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$363FlexibilityNo cancel feeOn-timeN/A

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