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$80+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Jun 22 — Jun 291
Sun 6/22
Sun 6/29
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 June 17, 2025.

Round-trip from

$158
(Frontier)

One-way from

$80
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$396

Good round-trip deal

$407 or less

Good one-way deal

$264 or less
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. 12% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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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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 June 17, 2025.

This Frontier deal was found by Cheapflights users on 6/14. 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 7/28:21 pmDEN - ORD
Nonstop2h 38mFrontier
Fri 7/45:40 amORD - DEN
Nonstop2h 52mFrontier
Deal found 6/14$158
This Frontier deal was found by Cheapflights users on 6/15. 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.
Mon 6/308:15 amDEN - MDW
Nonstop2h 25mFrontier
Fri 7/412:35 pmMDW - DEN
Nonstop2h 48mFrontier
Deal found 6/15$158
This Southwest deal was found by Cheapflights users on 6/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/65:50 amDEN - MDW
Nonstop2h 20mSouthwest
Sat 8/97:25 pmMDW - DEN
Nonstop2h 40mSouthwest
Deal found 6/15$159
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/188:28 pmDEN - ORD
Nonstop2h 31mUnited Airlines
Tue 9/237:15 amORD - DEN
Nonstop2h 44mUnited Airlines
Deal found 6/16$163
This American Airlines deal was found by Cheapflights users on 6/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/65:31 pmDEN - ORD
Nonstop2h 46mAmerican Airlines
Mon 8/117:10 amORD - DEN
Nonstop2h 41mAmerican Airlines
Deal found 6/16$165
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/191:15 pmDEN - ORD
Nonstop2h 30mSouthwest
Wed 8/201:50 pmORD - DEN
1 stop7h 10mSouthwest
Deal found 6/16$173
This FlightHub deal was found by Cheapflights users on 6/14. 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.
Wed 7/28:19 pmSLC - ORD
1 stop8h 53mSpirit Airlines
Mon 7/711:50 amORD - SLC
1 stop8h 34mSpirit Airlines
Deal found 6/14$195
This Priceline deal was found by Cheapflights users on 6/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/302:45 pmSLC - ORD
1 stop8h 14mFrontier
Thu 7/35:40 amORD - SLC
1 stop8h 30mFrontier
Deal found 6/16$200
This Frontier deal was found by Cheapflights users on 6/15. 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.
Sat 6/2812:26 pmSLC - MDW
1 stop7h 27mFrontier
Thu 7/32:44 pmMDW - SLC
1 stop10h 19mFrontier
Deal found 6/15$200
This FlightHub deal was found by Cheapflights users on 6/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/109:52 pmSLC - ORD
1 stop7h 11mMultiple Airlines
Tue 7/157:00 amORD - SLC
1 stop7h 09mMultiple Airlines
Deal found 6/15$203
This Delta deal was found by Cheapflights users on 6/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/612:55 amDEN - MDW
1 stop6h 49mDelta
Mon 8/117:17 pmMDW - DEN
1 stop4h 50mDelta
Deal found 6/17$217
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/86:05 amDEN - ORD
1 stop5h 45mDelta
Fri 7/115:08 pmORD - DEN
1 stop6h 58mDelta
Deal found 6/16$224

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 June 17, 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 7/2

8:21 pm-11:59 pm

Nonstop2h 38m

Chicago O'Hare Intl

Fri 7/4

5:40 am-7:32 am

Nonstop2h 52m

$158

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 6/30

8:15 am-11:40 am

Nonstop2h 25m

Chicago Midway

Fri 7/4

12:35 pm-2:23 pm

Nonstop2h 48m

$158

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 8/6

5:50 am-9:10 am

Nonstop2h 20m

Chicago Midway

Sat 8/9

7:25 pm-9:05 pm

Nonstop2h 40m

$159

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 8/6

5:31 pm-9:17 pm

Nonstop2h 46m

Chicago O'Hare Intl

Mon 8/11

7:10 am-8:51 am

Nonstop2h 41m

$165

DenverChicago

DEN - ORD

DENORD

Denver Intl

Tue 8/19

1:15 pm-4:45 pm

Nonstop2h 30m

Chicago O'Hare Intl

Wed 8/20

1:50 pm-8:00 pm

1 stop7h 10m

$173

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 7/23

7:50 am-11:25 am

Nonstop2h 35m

Chicago O'Hare Intl

Tue 7/29

5:00 am-6:43 am

Nonstop2h 43m

$177

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Wed 7/2

8:19 pm-6:12 am

1 stop8h 53m

Chicago O'Hare Intl

Mon 7/7

11:50 am-7:24 pm

1 stop8h 34m

$195

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Mon 6/30

2:45 pm-11:59 pm

1 stop8h 14m

Chicago O'Hare Intl

Thu 7/3

5:40 am-1:10 pm

1 stop8h 30m

$200

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Sat 6/28

12:26 pm-8:53 pm

1 stop7h 27m

Chicago Midway

Thu 7/3

2:44 pm-12:03 am

1 stop10h 19m

$200

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Thu 7/10

9:52 pm-6:03 am

1 stop7h 11m

Chicago O'Hare Intl

Tue 7/15

7:00 am-1:09 pm

1 stop7h 09m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

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.

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 June 17, 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 June 17, 2025.

The most flights from USWY to CHI are scheduled on a Monday (10 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (5 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 June 17, 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
10,000 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

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
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

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
4,279 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

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
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,503 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

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
8,801 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.1

Overall

8.0

Comfort

7.8

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 American Airlines, which is currently one of the cheapest options available, starting at $80. Southwest flights start at $80 while deals on United Airlines start at $85 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 United Airlines (94%), Lufthansa (94%) or Copa Airlines (93%) 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 $173. On average you can expect to pay $397. The most popular route, (Denver Intl - Chicago O'Hare Intl), can usually be booked for $131.

  • 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
Lansing
Benton Harbor
Porter
Hammond
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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Dallas/Fort Worth to Midway flights
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Tampa to O'Hare Intl flights
Philadelphia to Midway flights
Hobby to Midway flights
San Jose to O'Hare Intl flights
Hartford to O'Hare Intl flights
Baltimore to Midway flights
Minneapolis to Midway flights
Minneapolis to O'Hare Intl flights
Seattle to Midway flights
Newark to St. Louis flights
Oakland to O'Hare Intl flights
LaGuardia to St. Louis flights
Reagan-National 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 June 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$275Average$441FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$329Average$421FlexibilityNo cancel feeOn-time71%

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