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$62+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Frontier deal was found by Cheapflights users on 12/15. 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 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Fri 1/94:30 pmORD - DEN
Nonstop3h 01mFrontier
Deal found 12/15$103
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mMultiple Airlines
Wed 1/74:38 pmORD - DEN
1 stop9h 45mMultiple Airlines
Deal found 12/15$119
This Frontier deal was found by Cheapflights users on 12/15. 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 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Thu 1/88:00 amORD - DEN
1 stop12h 59mFrontier
Deal found 12/15$120
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Wed 12/318:45 pmDEN - ORD
Nonstop2h 27mMultiple Airlines
Tue 1/67:57 pmORD - DEN
1 stop16h 29mMultiple Airlines
Deal found 12/15$124
This Frontier deal was found by Cheapflights users on 12/15. 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.
Tue 12/307:00 amDEN - MDW
1 stop5h 59mFrontier
Thu 1/812:41 pmMDW - DEN
1 stop9h 57mFrontier
Deal found 12/15$130
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Sun 1/410:49 pmORD - DEN
1 stop30h 09mFrontier
Deal found 12/16$137
This Frontier deal was found by Cheapflights users on 12/15. 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.
Thu 12/258:45 pmDEN - ORD
Nonstop2h 27mFrontier
Fri 1/21:27 pmORD - DEN
1 stop11h 58mFrontier
Deal found 12/15$145
This Frontier deal was found by Cheapflights users on 12/15. 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.
Tue 12/307:00 amDEN - MDW
1 stop5h 59mFrontier
Fri 1/93:05 pmMDW - DEN
Nonstop2h 49mFrontier
Deal found 12/15$145
This Frontier deal was found by Cheapflights users on 12/15. 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.
Thu 12/258:45 pmDEN - ORD
Nonstop2h 27mFrontier
Thu 1/17:00 amORD - DEN
Nonstop2h 56mFrontier
Deal found 12/15$153
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:45 pmDEN - ORD
Nonstop2h 27mFrontier
Fri 1/212:26 pmORD - DEN
1 stop20h 49mFrontier
Deal found 12/16$156
This Frontier deal was found by Cheapflights users on 12/17. 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 12/318:45 pmDEN - ORD
Nonstop2h 27mFrontier
Sat 1/312:39 pmORD - DEN
1 stop10h 29mFrontier
Deal found 12/17$165
This Kiwi.com deal was found by Cheapflights users on 12/15. 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.
Tue 12/307:00 amDEN - MDW
1 stop5h 59mFrontier
Tue 1/62:03 pmMDW - DEN
1 stop8h 32mFrontier
Deal found 12/15$167

Find flight deals from Wyoming to Chicago

Keep the following information in mind while searching for Wyoming to Chicago flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$89
(Mytrip)

One-way from

$62
(Trip.com)

Popular in

January

Cheapest in

September

Average price

$529

Good round-trip deal

$433 or less

Good one-way deal

$259 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. 10% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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).
Search Deals

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 December 18, 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 - MDW

DENMDW

Denver Intl

Fri 1/16

4:32 pm-7:54 pm

Nonstop2h 22m

Chicago Midway

Mon 1/19

6:10 am-12:21 pm

1 stop7h 11m

$144

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 1/9

9:44 am-11:09 pm

1 stop12h 25m

Chicago Midway

Mon 1/12

3:00 pm-4:49 pm

Nonstop2h 49m

$159

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 1/17

11:20 am-2:55 pm

Nonstop2h 35m

Chicago O'Hare Intl

Mon 1/19

1:55 pm-3:52 pm

Nonstop2h 57m

$175

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 1/21

3:15 pm-6:46 pm

Nonstop2h 31m

Chicago O'Hare Intl

Sat 1/24

3:59 pm-5:57 pm

Nonstop2h 58m

$176

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 2/14

8:25 pm-11:45 pm

Nonstop2h 20m

Chicago Midway

Sun 2/15

2:05 pm-3:45 pm

Nonstop2h 40m

$177

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 1/10

5:42 pm-9:15 pm

Nonstop2h 33m

Chicago O'Hare Intl

Wed 1/14

2:36 pm-4:34 pm

Nonstop2h 58m

$183

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 1/8

9:40 am-1:24 pm

Nonstop2h 44m

Chicago O'Hare Intl

Tue 1/13

2:36 pm-4:34 pm

Nonstop2h 58m

$187

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 2/18

6:00 am-1:30 pm

1 stop6h 30m

Chicago O'Hare Intl

Wed 2/25

1:45 pm-9:05 pm

2 stops8h 20m

$190

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 2/14

1:33 pm-9:08 pm

1 stop6h 35m

Chicago Midway

Sun 2/15

3:26 pm-12:42 am

1 stop10h 16m

$190

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 12/24

5:45 pm-9:19 pm

Nonstop2h 34m

Chicago O'Hare Intl

Thu 12/25

8:45 am-10:35 am

Nonstop2h 50m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

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 July is currently the most expensive (average of $447). 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 December 18, 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.

Weekly flight availability from Wyoming to Chicago

Explore weekly flight availability from Wyoming to Chicago. 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 December 18, 2025.

The most flights from USWY to CHI are scheduled on a Thursday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

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

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 2h 20m. Frontier provides one of the quickest options available for as low as $177. Airlines will cover a distance of 893 mi. Most flights are nonstop.

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

    To fly one-way, consider booking your trip with TAP AIR PORTUGAL, which is currently one of the cheapest options available, starting at $387. United Airlines flights start at $425 while deals on Turkish Airlines start at $536 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 Qatar Airways (89%), American Airlines (82%) or United Airlines (68%) 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 $195. On average you can expect to pay $416. The most popular route, (Denver Intl - Chicago O'Hare Intl), can usually be booked for $119.

  • 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 July is currently the most expensive (average of $447). 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
Lansing
Merrillville
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.
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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$191Average$385FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$283Average$421FlexibilityNo cancel feeOn-time69%

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