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$63+ 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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$116
(CheapOair)

One-way from

$63
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$289

Good round-trip deal

$368 or less

Good one-way deal

$305 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. 6% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 15, 2025.

This CheapOair deal was found by Cheapflights users on 9/13. 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.
vie. 10/109:19 pmDEN - ORD
Nonstop2h 40mFrontier
vie. 10/176:42 pmORD - DEN
1 stop6h 30mFrontier
Deal found 9/13$116
This CheapOair deal was found by Cheapflights users on 9/13. 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.
lun. 10/277:49 amDEN - MDW
Nonstop2h 27mFrontier
vie. 10/311:37 pmMDW - DEN
1 stop8h 53mFrontier
Deal found 9/13$116
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
sáb. 9/275:50 pmDEN - ORD
Nonstop2h 38mFrontier
mar. 9/307:20 amORD - DEN
Nonstop2h 53mFrontier
Deal found 9/13$117
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/68:05 amDEN - MDW
Nonstop2h 25mFrontier
dom. 11/96:30 amMDW - DEN
1 stop26h 06mFrontier
Deal found 9/14$117
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/78:22 pmDEN - ORD
Nonstop2h 31mFrontier
mar. 10/147:15 amORD - DEN
Nonstop2h 49mFrontier
Deal found 9/15$118
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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.
mar. 10/712:36 amDEN - ORD
1 stop13h 32mFrontier
mar. 10/147:15 amORD - DEN
Nonstop2h 49mFrontier
Deal found 9/13$119
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/148:05 amDEN - MDW
Nonstop2h 25mFrontier
dom. 11/1612:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/14$119
This Gotogate deal was found by Cheapflights users on 9/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/118:22 pmDEN - ORD
Nonstop2h 31mFrontier
dom. 10/125:50 amORD - DEN
1 stop20h 01mFrontier
Deal found 9/14$120
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/78:05 amDEN - MDW
Nonstop2h 25mFrontier
vie. 11/1412:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/14$120
This Frontier deal was found by Cheapflights users on 9/14. 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.
mié. 10/15:50 pmDEN - ORD
Nonstop2h 38mFrontier
vie. 10/310:42 amORD - DEN
Nonstop2h 51mFrontier
Deal found 9/14$122
This Frontier deal was found by Cheapflights users on 9/13. 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.
mié. 10/2212:36 amDEN - MDW
1 stop8h 11mFrontier
vie. 10/3112:30 pmMDW - DEN
Nonstop2h 46mFrontier
Deal found 9/13$122
This Frontier deal was found by Cheapflights users on 9/14. 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.
mié. 10/15:50 pmDEN - ORD
Nonstop2h 38mFrontier
jue. 10/22:07 pmORD - DEN
1 stop8h 05mFrontier
Deal found 9/14$123

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 septiembre 15, 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

mar. 11/4

10:15 am-5:15 pm

1 stop6h 00m

Chicago Midway

jue. 11/6

9:40 pm-11:15 pm

Nonstop2h 35m

$152

DenverChicago

DEN - ORD

DENORD

Denver Intl

mié. 12/3

6:00 am-9:40 am

Nonstop2h 40m

Chicago O'Hare Intl

lun. 12/8

8:07 pm-9:56 pm

Nonstop2h 49m

$157

DenverChicago

DEN - ORD

DENORD

Denver Intl

jue. 10/16

4:45 pm-8:25 pm

Nonstop2h 40m

Chicago O'Hare Intl

lun. 10/20

9:44 pm-11:30 pm

Nonstop2h 46m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

sáb. 10/18

8:15 am-11:40 am

Nonstop2h 25m

Chicago Midway

lun. 10/20

9:50 pm-11:25 pm

Nonstop2h 35m

$157

DenverChicago

DEN - MDW

DENMDW

Denver Intl

mar. 10/7

1:30 pm-7:25 pm

1 stop4h 55m

Chicago Midway

sáb. 10/11

12:20 pm-2:00 pm

Nonstop2h 40m

$167

DenverChicago

DEN - MDW

DENMDW

Denver Intl

mar. 10/7

7:55 am-12:40 pm

1 stop3h 45m

Chicago Midway

mar. 10/7

8:40 pm-10:20 pm

Nonstop2h 40m

$167

DenverChicago

DEN - ORD

DENORD

Denver Intl

mar. 10/7

6:00 am-3:20 pm

2 stops8h 20m

Chicago O'Hare Intl

mar. 10/7

6:55 pm-8:55 pm

Nonstop3h 00m

$172

DenverChicago

DEN - MDW

DENMDW

Denver Intl

jue. 11/13

8:45 pm-12:05 am

Nonstop2h 20m

Chicago Midway

dom. 11/16

7:45 am-9:25 am

Nonstop2h 40m

$177

DenverChicago

DEN - MDW

DENMDW

Denver Intl

sáb. 10/25

5:25 pm-8:45 pm

Nonstop2h 20m

Chicago Midway

dom. 10/26

7:45 am-9:25 am

Nonstop2h 40m

$177

DenverChicago

DEN - MDW

DENMDW

Denver Intl

sáb. 2/14

4:40 pm-8:00 pm

Nonstop2h 20m

Chicago Midway

vie. 2/20

3:45 pm-9:10 pm

1 stop6h 25m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 septiembre 15, 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 septiembre 15, 2025.

The most flights from USWY to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

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 40m. Southwest provides one of the quickest options available for as low as $157. Airlines will cover a distance of 886 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $79. Southwest flights start at $79 while deals on Frontier start at $114 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 United Airlines (75%), Lufthansa (72%) or Emirates (72%) 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 $167. On average you can expect to pay $771. The most popular route, (Denver Intl - Chicago O'Hare Intl), can usually be booked for $120.

  • 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$229Average$404FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$297Average$461FlexibilityNo cancel feeOn-time69%

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