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$67+ Cheap flights from Wyoming 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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find flight deals from Wyoming to Chicago

Cheapest flights from Wyoming to Chicago
Explore the most affordable flight options available from Wyoming to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1012:59 amDEN - ORD
1 stop9h 15mFrontier
Tue 11/186:05 pmORD - DEN
Nonstop2h 54mFrontier
Deal found 10/29$115
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1212:05 pmDEN - ORD
Nonstop2h 34mFrontier
Wed 11/196:05 pmORD - DEN
Nonstop2h 54mFrontier
Deal found 10/30$116
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:59 amDEN - ORD
1 stop15h 28mFrontier
Sun 12/77:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 10/30$117
This Priceline deal was found by Cheapflights users on 10/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:42 pmDEN - MDW
1 stop7h 30mFrontier
Mon 12/812:18 pmMDW - DEN
Nonstop2h 44mFrontier
Deal found 10/29$117
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/248:45 pmDEN - ORD
Nonstop2h 25mFrontier
Sun 12/79:52 pmORD - DEN
1 stop12h 03mFrontier
Deal found 10/29$118
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1912:59 amDEN - ORD
1 stop20h 37mFrontier
Mon 11/247:00 amORD - DEN
Nonstop3h 00mFrontier
Deal found 10/30$120
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/238:45 pmDEN - ORD
Nonstop2h 25mFrontier
Thu 12/117:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 10/30$121
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:59 pmDEN - ORD
Nonstop2h 30mFrontier
Wed 11/126:05 pmORD - DEN
Nonstop2h 54mFrontier
Deal found 10/29$122
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/51:42 pmDEN - MDW
1 stop7h 30mFrontier
Sun 12/712:18 pmMDW - DEN
Nonstop2h 44mFrontier
Deal found 10/29$122
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1112:05 pmDEN - ORD
Nonstop2h 34mFrontier
Sat 11/157:15 amORD - DEN
Nonstop2h 49mFrontier
Deal found 10/29$123
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/512:59 amDEN - MDW
1 stop12h 00mFrontier
Sun 12/72:01 pmMDW - DEN
1 stop19h 26mFrontier
Deal found 10/30$124
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:45 pmDEN - ORD
Nonstop2h 27mMultiple Airlines
Tue 12/169:06 pmORD - DEN
1 stop14h 06mMultiple Airlines
Deal found 10/30$125

Cheap flight deals from Wyoming to Chicago

Keep the following information in mind while searching for Wyoming to Chicago flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$115
(Frontier)

One-way from

$67
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$425

Good round-trip deal

$413 or less

Good one-way deal

$275 or less
Provider with most accurate pricing for Jackson Hole-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Jackson Hole-Chicago (CHI) flights.
Search Deals
From Wyoming to Chicago (CHI)
Search Deals
One-way flight from Wyoming to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($164 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($56 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 Wyoming to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Wyoming to Chicago (CHI).
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Wyoming 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 October 30, 2025.
Use the filters below to find and compare flights from Wyoming to Chicago that are best for you.

Fly from

Wyoming

Fly to

Chicago

Route

Depart

Return

Price

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 12/3

12:59 am-5:27 pm

1 stop15h 28m

Chicago O'Hare Intl

Mon 12/8

3:23 pm-10:59 pm

1 stop8h 36m

$129

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 11/21

8:45 pm-12:10 am

Nonstop2h 25m

Chicago O'Hare Intl

Mon 11/24

7:00 am-9:00 am

Nonstop3h 00m

$145

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 12/3

12:59 am-3:47 pm

2 stops13h 48m

Chicago O'Hare Intl

Mon 12/8

3:23 pm-10:59 pm

1 stop8h 36m

$163

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 12/12

9:16 pm-11:54 am

2 stops13h 38m

Chicago O'Hare Intl

Mon 12/15

3:23 pm-10:59 pm

1 stop8h 36m

$179

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Fri 12/5

10:22 am-10:12 pm

2 stops10h 50m

Chicago Midway

Sun 12/7

12:18 pm-9:27 am

1 stop22h 09m

$179

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 12/8

8:05 am-12:35 pm

1 stop3h 30m

Chicago Midway

Mon 12/22

10:30 pm-12:10 am

Nonstop2h 40m

$183

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Fri 12/5

10:22 am-10:24 pm

2 stops11h 02m

Chicago O'Hare Intl

Sun 12/7

9:52 pm-7:41 am

1 stop10h 49m

$185

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Thu 11/13

8:10 pm-11:30 am

1 stop14h 20m

Chicago Midway

Mon 11/17

12:30 pm-11:40 am

1 stop24h 10m

$185

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/16

5:25 am-8:55 am

Nonstop2h 30m

Chicago Midway

Mon 1/19

9:55 am-2:30 pm

1 stop5h 35m

$186

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 12/11

12:59 am-2:21 pm

2 stops12h 22m

Chicago O'Hare Intl

Mon 12/15

7:00 am-8:56 am

Nonstop2h 56m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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

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

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

Currently, September is the cheapest month in which you can book a flight from Wyoming to Chicago (average of $197). Flying from Wyoming to Chicago in December is currently the most expensive (average of $486). 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 WY to CHI?

Find hourly flight availability from Wyoming to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Wyoming to Chicago. 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 Wyoming to Chicago?

    A quick flight from Wyoming to Chicago can take about 3h 30m. Frontier provides one of the quickest options available for as low as $183. Airlines will cover a distance of 893 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $69. United Airlines flights start at $78 while deals on Southwest start at $78 one-way.

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

    While some choose either Denver Intl - Chicago Midway or Salt Lake City - Chicago O'Hare Intl, Denver Intl - Chicago O'Hare Intl is the most popular route from Wyoming to Chicago.

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

    No one likes to see their flight delayed. When booking a flight from Wyoming to Chicago consider choosing Emirates (85%), Lufthansa (77%) or Qatar Airways (70%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Wyoming to Chicago?

    The cheapest flight price from Wyoming to Chicago is $134. On average you can expect to pay $463. The most popular route, (Denver Intl - Chicago O'Hare Intl), can usually be booked for $69.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Wyoming 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.

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

    Currently, September is the cheapest month in which you can book a flight from Wyoming to Chicago (average of $197). Flying from Wyoming to Chicago in December is currently the most expensive (average of $486). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Wyoming to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
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LaGuardia to Midway flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Newark to St. Louis flights
Denver to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
Raleigh to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
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Love Field to O'Hare Intl flights
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Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Portland to O'Hare Intl flights
LaGuardia to St. Louis flights
Boston to Midway flights

Top 2 airlines flying from Wyoming to Chicago

Discover the top 2 airlines that operate flights from Wyoming to Chicago. 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$385FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$297Average$434FlexibilityNo cancel feeOn-time69%

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