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$76+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$130
(Kiwi.com)

One-way from

$76
(Southwest)

Popular in

March

Cheapest in

December

Average price

$605

Good round-trip deal

$399 or less

Good one-way deal

$269 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. 1% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Fri 6/278:21 pmDEN - ORD
Nonstop2h 38mFrontier
Mon 6/305:40 amORD - DEN
Nonstop2h 52mFrontier
Deal found 4/30$130
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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.
Thu 5/153:42 pmDEN - MDW
Nonstop2h 26mFrontier
Tue 5/272:44 pmMDW - DEN
Nonstop2h 49mFrontier
Deal found 4/29$149
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:30 pmDEN - ORD
Nonstop2h 35mSouthwest
Sun 5/2512:40 pmORD - DEN
Nonstop2h 45mSouthwest
Deal found 4/30$151
This Southwest deal was found by Cheapflights users on 4/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/134:50 pmDEN - MDW
Nonstop2h 20mSouthwest
Wed 8/206:00 amMDW - DEN
Nonstop2h 35mSouthwest
Deal found 4/30$151
This United Airlines deal was found by Cheapflights users on 5/1. 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.
Wed 6/44:17 pmDEN - ORD
Nonstop2h 43mUnited Airlines
Sat 6/76:32 pmORD - DEN
Nonstop3h 01mUnited Airlines
Deal found 5/1$160
This Mytrip deal was found by Cheapflights users on 4/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/288:14 pmSLC - ORD
1 stop13h 41mSpirit Airlines
Wed 6/411:50 amORD - SLC
1 stop8h 29mSpirit Airlines
Deal found 4/30$164
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Mon 7/288:33 amDEN - ORD
1 stop7h 36mMultiple Airlines
Thu 8/75:40 amORD - DEN
Nonstop2h 50mMultiple Airlines
Deal found 5/1$166
This American Airlines deal was found by Cheapflights users on 5/1. 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 6/257:21 amDEN - ORD
Nonstop2h 40mAmerican Airlines
Mon 6/306:49 amORD - DEN
Nonstop2h 34mAmerican Airlines
Deal found 5/1$173
This Frontier deal was found by Cheapflights users on 4/30. 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.
Sat 5/312:03 pmSLC - MDW
1 stop5h 50mFrontier
Tue 6/32:44 pmMDW - SLC
1 stop9h 24mFrontier
Deal found 4/30$198
This American Airlines deal was found by Cheapflights users on 5/1. 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.
Fri 6/61:10 pmJAC - ORD
Nonstop3h 02mAmerican Airlines
Thu 6/121:22 pmORD - JAC
Nonstop3h 06mAmerican Airlines
Deal found 5/1$211
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2412:55 amDEN - ORD
1 stop5h 54mDelta
Wed 7/23:52 pmORD - DEN
1 stop5h 36mDelta
Deal found 4/30$217
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/126:20 amDEN - MDW
1 stop5h 09mDelta
Tue 6/179:21 amMDW - DEN
1 stop7h 13mDelta
Deal found 4/30$217

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 May 1, 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

Fri 6/27

8:21 pm-11:59 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 6/30

5:40 am-7:32 am

Nonstop2h 52m

$130

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 5/15

3:42 pm-7:08 pm

Nonstop2h 26m

Chicago Midway

Tue 5/27

2:44 pm-4:33 pm

Nonstop2h 49m

$149

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 5/24

7:30 pm-11:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Sun 5/25

12:40 pm-2:25 pm

Nonstop2h 45m

$151

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 8/13

4:50 pm-8:10 pm

Nonstop2h 20m

Chicago Midway

Wed 8/20

6:00 am-7:35 am

Nonstop2h 35m

$151

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 6/4

4:17 pm-8:00 pm

Nonstop2h 43m

Chicago O'Hare Intl

Sat 6/7

6:32 pm-8:33 pm

Nonstop3h 01m

$160

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Wed 5/28

8:14 pm-10:55 am

1 stop13h 41m

Chicago O'Hare Intl

Wed 6/4

11:50 am-7:19 pm

1 stop8h 29m

$164

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 6/14

10:27 am-9:39 pm

1 stop10h 12m

Chicago O'Hare Intl

Sun 6/15

9:05 am-10:58 am

Nonstop2h 53m

$168

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 6/25

7:21 am-11:01 am

Nonstop2h 40m

Chicago O'Hare Intl

Mon 6/30

6:49 am-8:23 am

Nonstop2h 34m

$173

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Sat 5/31

2:03 pm-8:53 pm

1 stop5h 50m

Chicago Midway

Tue 6/3

2:44 pm-11:08 pm

1 stop9h 24m

$198

JacksonChicago

JAC - ORD

JACORD

Jackson Hole

Fri 6/6

1:10 pm-5:12 pm

Nonstop3h 02m

Chicago O'Hare Intl

Thu 6/12

1:22 pm-3:28 pm

Nonstop3h 06m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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, 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.

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 May 1, 2025.
Read through reviews of airlines operating flights from Wyoming to Chicago, such as Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,293 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,409 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Overall

8.0

Food

7.1

Boarding

8.1

Entertainment

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Southwest, which is currently one of the cheapest options available, starting at $76. United Airlines flights start at $85 while deals on Frontier start at $89 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 (89%), Lufthansa (89%) or United Airlines (67%) 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 $193. On average you can expect to pay $604. The most popular route, (Denver Intl - Chicago O'Hare Intl), can usually be booked for $104.

  • 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
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.
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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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$275Average$443FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$421FlexibilityNo cancel feeOn-time71%

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