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$58+ 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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$77
(Frontier)

One-way from

$58
(Frontier)

Popular in

July

Cheapest in

December

Average price

$359

Good round-trip deal

$496 or less

Good one-way deal

$288 or less
Provider with most accurate pricing for Jackson Hole-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Jackson Hole-Chicago (CHI) flights.
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From Wyoming to Chicago (CHI)
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One-way flight from Wyoming to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Price to beat on a round-trip flight from Wyoming to Chicago (CHI).
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Price to beat on a one-way flight from Wyoming to Chicago (CHI).
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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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/249:08 pmDEN - ORD
Nonstop2h 36mFrontier
Sun 3/306:50 amORD - DEN
Nonstop3h 03mFrontier
Deal found 2/19$77
This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/248:55 pmDEN - MDW
Nonstop2h 22mFrontier
Sun 3/306:40 amMDW - DEN
Nonstop2h 52mFrontier
Deal found 2/19$77
This Trip.com deal was found by Cheapflights users on 2/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/105:19 pmSLC - ORD
Nonstop3h 14mFrontier
Wed 3/126:45 amORD - SLC
1 stop18h 55mFrontier
Deal found 2/20$102
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/188:49 pmSLC - ORD
Nonstop3h 14mMultiple Airlines
Tue 4/228:00 amORD - SLC
1 stop6h 29mMultiple Airlines
Deal found 2/18$124
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/123:07 pmSLC - MDW
1 stop8h 10mFrontier
Mon 3/178:44 pmMDW - SLC
1 stop12h 46mFrontier
Deal found 2/20$125
This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/152:36 pmSLC - ORD
1 stop14h 57mSpirit Airlines
Tue 4/228:00 amORD - SLC
1 stop6h 29mSpirit Airlines
Deal found 2/18$138
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:00 amDEN - ORD
Nonstop2h 32mAmerican Airlines
Sat 5/103:24 pmORD - DEN
Nonstop2h 43mAmerican Airlines
Deal found 2/20$159
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/77:25 pmDEN - MDW
Nonstop2h 25mSouthwest
Sat 5/108:35 pmMDW - DEN
Nonstop2h 45mSouthwest
Deal found 2/20$159
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/247:30 pmDEN - ORD
Nonstop2h 35mSouthwest
Sat 4/267:00 amORD - DEN
Nonstop2h 40mSouthwest
Deal found 2/20$164
This Booking.com deal was found by Cheapflights users on 2/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1912:16 pmDEN - ORD
1 stop5h 55mMultiple Airlines
Mon 6/235:35 amORD - DEN
Nonstop2h 52mMultiple Airlines
Deal found 2/19$192
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/313:20 pmDEN - ORD
Nonstop2h 26mUnited Airlines
Sun 11/27:15 amORD - DEN
Nonstop2h 40mUnited Airlines
Deal found 2/19$205
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/36:23 amDEN - ORD
1 stop5h 18mDelta
Mon 4/75:00 pmORD - DEN
1 stop5h 38mDelta
Deal found 2/20$216

Find flights from Wyoming to Chicago within your budget

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 February 20, 2025.

Fly from

Wyoming

Fly to

Chicago

Route

Depart

Return

Price

DenverChicago

DEN - ORD

DENORD

Denver Intl

Mon 3/24

9:08 pm-12:44 am

Nonstop2h 36m

Chicago O'Hare Intl

Sun 3/30

6:50 am-8:53 am

Nonstop3h 03m

$77

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 3/24

8:55 pm-12:17 am

Nonstop2h 22m

Chicago Midway

Sun 3/30

6:40 am-8:32 am

Nonstop2h 52m

$77

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Mon 3/10

5:19 pm-9:33 pm

Nonstop3h 14m

Chicago O'Hare Intl

Wed 3/12

6:45 am-12:40 am

1 stop18h 55m

$102

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Fri 4/18

8:49 pm-1:03 am

Nonstop3h 14m

Chicago O'Hare Intl

Tue 4/22

8:00 am-1:29 pm

1 stop6h 29m

$124

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Wed 3/12

3:07 pm-12:17 am

1 stop8h 10m

Chicago Midway

Mon 3/17

8:44 pm-8:30 am

1 stop12h 46m

$125

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Tue 4/15

2:36 pm-6:33 am

1 stop14h 57m

Chicago O'Hare Intl

Tue 4/22

8:00 am-1:29 pm

1 stop6h 29m

$138

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 5/7

1:45 pm-5:31 pm

Nonstop2h 46m

Chicago O'Hare Intl

Sat 5/10

9:20 pm-11:08 pm

Nonstop2h 48m

$159

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 5/7

7:25 pm-10:50 pm

Nonstop2h 25m

Chicago Midway

Sat 5/10

8:35 pm-10:20 pm

Nonstop2h 45m

$159

DenverChicago

DEN - ORD

DENORD

Denver Intl

Thu 4/24

7:30 pm-11:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sat 4/26

7:00 am-8:40 am

Nonstop2h 40m

$164

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 2/28

6:08 pm-8:56 pm

1 stop25h 48m

Chicago O'Hare Intl

Fri 3/7

6:30 am-8:33 am

Nonstop3h 03m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 51 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.

Travel insights for flights from Wyoming to Chicago

Get recent, data-driven insights about flights from Wyoming to Chicago including ideal travel times, pricing trends, and more.

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

Currently, August is the cheapest month in which you can book a flight from Wyoming to Chicago (average of $245). Flying from Wyoming to Chicago in March is currently the most expensive (average of $321). 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 February 20, 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 February 20, 2025.

The most flights from USWY to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated February 20, 2025.
Read through reviews of airlines operating flights from Wyoming to Chicago, such as Southwest, Alaska Airlines and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

  • 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 $58. Spirit Airlines flights start at $78 while deals on Southwest start at $80 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 (78%), Lufthansa (76%) or United Airlines (39%) 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 $202. On average you can expect to pay $666. 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, August is the cheapest month in which you can book a flight from Wyoming to Chicago (average of $245). Flying from Wyoming to Chicago in March is currently the most expensive (average of $321). 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 Wyoming?

Book flights to Wyoming if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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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Reagan-National to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
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Sky Harbor Intl to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Baltimore to Midway flights
Austin to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Reagan-National to Midway flights
Raleigh to O'Hare Intl flights
Burbank to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Orlando to O'Hare Intl flights
Love Field to O'Hare Intl flights
Miami to O'Hare Intl flights
Seattle to Midway flights
Atlanta to Midway flights
Newark to St. Louis flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
LaGuardia to St. Louis flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Dulles Intl to St. Louis flights
Denver 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$275Average$461FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$331Average$421FlexibilityNo cancel feeOn-time71%
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