HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$59+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wyoming to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$97
(Cheapflightsfares)

One-way from

$59
(Cheapflightsfares)

Popular in

September

Cheapest in

December

Average price

$489

Good round-trip deal

$538 or less

Good one-way deal

$284 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. 6% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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

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 April 2, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/38:22 pmDEN - ORD
Nonstop2h 37mFrontier
Tue 6/106:00 amORD - DEN
Nonstop2h 51mFrontier
Deal found 4/1$97
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/23:42 pmDEN - MDW
Nonstop2h 26mFrontier
Mon 5/58:03 pmMDW - DEN
Nonstop2h 53mFrontier
Deal found 4/1$97
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/118:50 pmSLC - ORD
Nonstop3h 09mFrontier
Mon 4/145:07 pmORD - SLC
Nonstop3h 43mFrontier
Deal found 4/1$134
This CheapOair deal was found by Cheapflights users on 4/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/218:14 pmSLC - ORD
1 stop8h 11mSpirit Airlines
Tue 5/2711:50 amORD - SLC
1 stop8h 29mSpirit Airlines
Deal found 4/1$144
This Southwest deal was found by Cheapflights users on 4/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/297:30 pmDEN - ORD
Nonstop2h 35mSouthwest
Wed 4/306:55 pmORD - DEN
Nonstop3h 00mSouthwest
Deal found 4/1$151
This Southwest deal was found by Cheapflights users on 3/31. 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.
Tue 4/298:30 amDEN - MDW
Nonstop2h 20mSouthwest
Tue 5/66:45 pmMDW - DEN
Nonstop2h 45mSouthwest
Deal found 3/31$151
This American Airlines deal was found by Cheapflights users on 4/1. 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.
Sat 5/37:20 amDEN - ORD
Nonstop2h 29mAmerican Airlines
Sat 5/31:36 pmORD - DEN
Nonstop2h 51mAmerican Airlines
Deal found 4/1$154
This United Airlines deal was found by Cheapflights users on 4/1. 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.
Sat 5/38:57 pmDEN - ORD
Nonstop2h 32mUnited Airlines
Thu 5/85:05 amORD - DEN
Nonstop2h 49mUnited Airlines
Deal found 4/1$164
This FlightHub deal was found by Cheapflights users on 4/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/110:14 amDEN - ORD
1 stop7h 57mMultiple Airlines
Tue 8/55:40 amORD - DEN
Nonstop2h 50mMultiple Airlines
Deal found 4/1$167
This Trip.com deal was found by Cheapflights users on 4/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/242:36 pmSLC - ORD
1 stop14h 57mMultiple Airlines
Mon 4/285:24 pmORD - SLC
1 stop8h 11mMultiple Airlines
Deal found 4/1$177
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/254:50 pmDEN - ORD
1 stop6h 09mDelta
Mon 4/286:59 pmORD - DEN
1 stop5h 10mDelta
Deal found 4/1$217
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2512:55 amDEN - MDW
1 stop6h 45mDelta
Tue 4/291:16 pmMDW - DEN
1 stop4h 52mDelta
Deal found 4/1$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 April 2, 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 5/2

8:11 pm-11:41 pm

Nonstop2h 30m

Chicago O'Hare Intl

Mon 5/5

5:21 pm-7:23 pm

Nonstop3h 02m

$97

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 5/2

3:42 pm-7:08 pm

Nonstop2h 26m

Chicago Midway

Mon 5/5

8:03 pm-9:56 pm

Nonstop2h 53m

$97

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Fri 4/11

8:50 pm-12:59 am

Nonstop3h 09m

Chicago O'Hare Intl

Mon 4/14

5:07 pm-7:50 pm

Nonstop3h 43m

$134

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Wed 5/21

8:14 pm-5:25 am

1 stop8h 11m

Chicago O'Hare Intl

Tue 5/27

11:50 am-7:19 pm

1 stop8h 29m

$144

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 4/22

7:20 am-10:49 am

Nonstop2h 29m

Chicago O'Hare Intl

Tue 4/29

1:36 pm-3:27 pm

Nonstop2h 51m

$151

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 4/29

8:30 am-11:50 am

Nonstop2h 20m

Chicago Midway

Tue 5/6

6:45 pm-8:30 pm

Nonstop2h 45m

$151

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 4/29

7:30 pm-11:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

Tue 5/6

6:55 pm-8:55 pm

Nonstop3h 00m

$159

DenverChicago

DEN - ORD

DENORD

Denver Intl

Sat 5/3

8:57 pm-12:29 am

Nonstop2h 32m

Chicago O'Hare Intl

Thu 5/8

5:05 am-6:54 am

Nonstop2h 49m

$164

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 7/4

10:14 am-7:11 pm

1 stop7h 57m

Chicago O'Hare Intl

Tue 7/29

5:40 am-7:30 am

Nonstop2h 50m

$168

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Thu 4/24

2:36 pm-6:33 am

1 stop14h 57m

Chicago O'Hare Intl

Mon 4/28

5:24 pm-12:35 am

1 stop8h 11m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 60 results
1
2
3
...
6

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 $323). 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 April 2, 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.

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 April 2, 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
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,820 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,272 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,898 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,615 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Allegiant Air
7.3
Good
731 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $59. United Airlines flights start at $76 while deals on Southwest start at $76 one-way.

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

    While some choose either Salt Lake City - Chicago O'Hare Intl or Denver Intl - Chicago Midway, 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 (88%), Lufthansa (82%) or United Airlines (80%) 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 $226. On average you can expect to pay $512. The most popular route, (Denver Intl - Chicago O'Hare Intl), can usually be booked for $130.

  • 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 $323). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wyoming to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Boston to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Seattle to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Denver to O'Hare Intl flights
San Francisco to Midway flights
Baltimore to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Diego to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Ontario to O'Hare Intl flights
Atlanta to O'Hare Intl flights
LaGuardia to Midway flights
Dulles Intl to Midway flights
Philadelphia to Midway flights
Orlando to O'Hare Intl flights
Newark to St. Louis flights
Minneapolis to Midway flights
Charlotte to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Austin to O'Hare Intl flights
Boston to Midway flights
Portland to O'Hare Intl flights
Reagan-National to Midway flights
Fort Lauderdale to O'Hare Intl flights
Atlanta to Midway flights
Hartford to O'Hare Intl flights
Seattle to Midway flights
Boston to St. Louis flights
Burbank to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Los Angeles to Midway flights
LaGuardia to St. Louis flights
Cleveland to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
Baltimore to Midway flights
Tampa to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Hobby to O'Hare Intl 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$275Average$471FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$424FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.