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$43+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — CHI
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Wyoming to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Wyoming (USWY) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$78
(Cheapflightsfares)

One-way from

$43
(Cheapflightsfares)
From Wyoming to Chicago (CHI)
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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 December 18, 2024.

This FlightHub deal was found by Cheapflights users on 12/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/256:10 pmDEN - MDW
Nonstop2h 22mFrontier
Wed 1/88:15 amMDW - DEN
Nonstop2h 52mFrontier
Deal found 12/17$83
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/258:10 pmDEN - ORD
Nonstop2h 36mFrontier
Fri 1/104:53 pmORD - DEN
1 stop8h 12mFrontier
Deal found 12/17$100
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/258:28 pmDEN - ORD
Nonstop2h 31mUnited Airlines
Tue 1/79:45 amORD - DEN
Nonstop2h 50mUnited Airlines
Deal found 12/17$174
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:10 pmDEN - ORD
1 stop13h 53mMultiple Airlines
Thu 1/97:25 amORD - DEN
Nonstop3h 01mMultiple Airlines
Deal found 12/17$182
This Delta deal was found by Cheapflights users on 12/17. 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.
Tue 12/314:19 pmDEN - ORD
1 stop5h 33mDelta
Wed 1/85:45 amORD - DEN
1 stop6h 27mDelta
Deal found 12/17$226
This Delta deal was found by Cheapflights users on 12/17. 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 12/2510:32 amDEN - MDW
1 stop4h 38mDelta
Wed 1/89:34 amMDW - DEN
1 stop5h 26mDelta
Deal found 12/17$226
This Kiwi.com deal was found by Cheapflights users on 12/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/279:08 pmSLC - ORD
1 stop24h 36mMultiple Airlines
Wed 1/89:54 pmORD - SLC
1 stop14h 20mMultiple Airlines
Deal found 12/17$231
This Mytrip deal was found by Cheapflights users on 12/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/246:29 pmSLC - MDW
1 stop26h 03mFrontier
Thu 1/28:41 pmMDW - SLC
1 stop13h 00mFrontier
Deal found 12/17$245
This American Airlines deal was found by Cheapflights users on 12/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/315:00 amDEN - ORD
1 stop5h 30mAmerican Airlines
Tue 1/75:00 amORD - DEN
1 stop7h 45mAmerican Airlines
Deal found 12/17$262
This Sun Country Air deal was found by Cheapflights users on 12/18. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3110:04 amDEN - ORD
1 stop6h 34mSun Country Air
Sun 1/58:03 pmORD - DEN
1 stop22h 27mSun Country Air
Deal found 12/18$270
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/316:30 pmDEN - MDW
Nonstop2h 20mSouthwest
Sun 1/510:40 pmMDW - DEN
Nonstop2h 40mSouthwest
Deal found 12/17$273
This Southwest deal was found by Cheapflights users on 12/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/317:05 pmDEN - ORD
Nonstop2h 30mSouthwest
Sun 1/57:30 amORD - DEN
2 stops6h 40mSouthwest
Deal found 12/17$283

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

DenverChicago

DEN - ORD

DENORD

Denver Intl

Fri 1/10

8:59 pm-12:35 am

Nonstop2h 36m

Chicago O'Hare Intl

Mon 1/13

7:50 am-9:51 am

Nonstop3h 01m

$78

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Fri 2/7

8:55 pm-12:17 am

Nonstop2h 22m

Chicago Midway

Sun 2/9

7:15 am-9:09 am

Nonstop2h 54m

$78

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 1/22

1:00 pm-4:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Wed 1/22

5:35 pm-7:16 pm

Nonstop2h 41m

$134

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 1/21

6:30 pm-9:45 pm

Nonstop2h 15m

Chicago Midway

Sat 1/25

7:20 pm-9:10 pm

Nonstop2h 50m

$140

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Thu 1/9

1:19 pm-10:07 pm

1 stop7h 48m

Chicago O'Hare Intl

Sun 1/12

6:36 pm-9:25 am

1 stop15h 49m

$148

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 1/15

8:29 pm-11:59 pm

Nonstop2h 30m

Chicago O'Hare Intl

Wed 1/22

7:10 am-9:00 am

Nonstop2h 50m

$149

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Fri 1/31

6:15 am-12:17 am

1 stop17h 02m

Chicago Midway

Sun 2/2

12:43 pm-9:34 am

1 stop21h 51m

$150

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Thu 1/23

1:21 pm-10:12 pm

1 stop7h 51m

Chicago O'Hare Intl

Tue 1/28

1:39 pm-11:14 am

1 stop22h 35m

$170

DenverChicago

DEN - ORD

DENORD

Denver Intl

Wed 1/15

7:05 pm-10:35 pm

Nonstop2h 30m

Chicago O'Hare Intl

Sun 1/19

5:45 pm-7:30 pm

Nonstop2h 45m

$175

Salt Lake CityChicago

SLC - ORD

SLCORD

Salt Lake City

Tue 1/14

12:09 pm-5:31 am

1 stop16h 22m

Chicago O'Hare Intl

Tue 1/21

1:39 pm-11:14 am

1 stop22h 35m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 58 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, September is the cheapest month in which you can book a flight from Wyoming to Chicago (average of $232). Flying from Wyoming to Chicago in June is currently the most expensive (average of $308). 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 December 18, 2024.

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 December 18, 2024.
Read through reviews of airlines operating flights from Wyoming to Chicago, such as American Airlines, Delta and Frontier. 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
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,554 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,279 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,055 reviews
Southwest
8.1
Very good
4,848 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $43. United Airlines flights start at $70 while deals on Southwest start at $70 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 (87%), Lufthansa (85%) or United Airlines (83%) 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 $197. On average you can expect to pay $539. The most popular route, (Denver Intl - Chicago O'Hare Intl), can usually be booked for $101.

  • 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, September is the cheapest month in which you can book a flight from Wyoming to Chicago (average of $232). Flying from Wyoming to Chicago in June is currently the most expensive (average of $308). 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.

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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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LaGuardia to St. Louis flights
Boston 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$275Average$447FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$365Average$411FlexibilityNo cancel feeOn-time71%
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