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$65+ Cheap flights from Wyoming to Midway (MDW)

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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — MDW
Apr 15 — Apr 221
Tue 4/15
Tue 4/22
1 adult, Economy
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Cheap flight deals from Wyoming to Midway

Keep the following information in mind while searching for Wyoming to Midway flight deals. Data was last updated April 10, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$126
(CheapOair)

One-way from

$65
(FlightHub)

Popular in

July

Cheapest in

December

Average price

$489
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 Midway
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One-way flight from Wyoming to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Wyoming to Midway

Cheapest flights from Wyoming to Midway
Explore the most affordable flight options available from Wyoming to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 10, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Sat 4/198:55 pmDEN - MDW
Nonstop2h 26mFrontier
Sun 4/206:45 amMDW - DEN
Nonstop2h 50mFrontier
Deal found 4/9$116
This Southwest deal was found by Cheapflights users on 4/9. 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 5/75:50 pmDEN - MDW
Nonstop2h 30mSouthwest
Sat 5/108:35 pmMDW - DEN
Nonstop2h 45mSouthwest
Deal found 4/9$151
This Frontier deal was found by Cheapflights users on 4/9. 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 4/1610:15 amSLC - MDW
1 stop9h 07mFrontier
Tue 4/2212:19 pmMDW - SLC
1 stop7h 36mFrontier
Deal found 4/9$178
This Delta deal was found by Cheapflights users on 4/9. 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 4/3012:55 amDEN - MDW
1 stop7h 12mDelta
Fri 5/21:16 pmMDW - DEN
1 stop4h 52mDelta
Deal found 4/9$217
This Southwest deal was found by Cheapflights users on 4/9. 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 5/77:30 amSLC - MDW
Nonstop3h 05mSouthwest
Wed 5/148:40 amMDW - SLC
Nonstop3h 30mSouthwest
Deal found 4/9$339
This Delta deal was found by Cheapflights users on 4/8. 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.
Sun 8/3111:00 amSLC - MDW
1 stop6h 03mDelta
Tue 9/99:20 amMDW - SLC
1 stop8h 12mDelta
Deal found 4/8$396
This Delta deal was found by Cheapflights users on 4/9. 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 4/177:05 amJAC - MDW
2 stops10h 15mDelta
Mon 4/2110:20 amMDW - JAC
2 stops9h 38mDelta
Deal found 4/9$429

Cheapflights Fare Finder

Customize your flight search to find flights from Wyoming to Midway 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 10, 2025.
Use the filters below to find and compare flights from Wyoming to Chicago Midway Airport that are best for you.

Fly from

Wyoming

Fly to

Midway

Route

Depart

Return

Price

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Sat 5/24

5:26 pm-8:53 pm

Nonstop2h 27m

Chicago Midway

Tue 5/27

2:44 pm-4:33 pm

Nonstop2h 49m

$126

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 5/7

5:50 pm-9:20 pm

Nonstop2h 30m

Chicago Midway

Sat 5/10

8:35 pm-10:20 pm

Nonstop2h 45m

$151

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Sat 5/3

2:57 pm-7:08 pm

1 stop27h 11m

Chicago Midway

Mon 5/5

6:15 am-11:33 am

1 stop6h 18m

$190

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 4/30

12:55 am-9:07 am

1 stop7h 12m

Chicago Midway

Fri 5/2

1:16 pm-5:08 pm

1 stop4h 52m

$217

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Wed 5/7

7:30 am-11:35 am

Nonstop3h 05m

Chicago Midway

Wed 5/14

8:40 am-11:10 am

Nonstop3h 30m

$339

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Sun 8/31

11:00 am-6:03 pm

1 stop6h 03m

Chicago Midway

Tue 9/9

9:20 am-4:32 pm

1 stop8h 12m

$396

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Wed 6/4

7:30 am-5:45 pm

2 stops9h 15m

Chicago Midway

Sat 6/7

9:16 am-6:12 pm

2 stops9h 56m

$529

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 6/17

5:26 pm-8:53 pm

Nonstop2h 27m

$65

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Tue 5/6

5:55 am-9:20 am

Nonstop2h 25m

$76

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Thu 5/1

6:00 am-7:08 pm

1 stop12h 08m

$88

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

Showing 1-10 of 17 results
1
2

Best time to book a flight from Wyoming to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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 Midway Airport

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport 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 Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, 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 Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated April 10, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and Allegiant Air from Wyoming to Chicago to help guide your decision. 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
8.0
Very good
4,278 reviews

Entertainment

7.6

Food

7.1

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Entertainment

7.6

Food

7.1

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,907 reviews
Southwest
8.0
Very good
4,278 reviews

Entertainment

7.6

Food

7.1

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,278 reviews

Entertainment

7.6

Food

7.1

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,279 reviews
Southwest
8.0
Very good
4,278 reviews

Entertainment

7.6

Food

7.1

Comfort

8.0

Crew

8.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Wyoming to Midway. 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 Midway Airport one-way?

    The cheapest airlines for a one-way flight from Wyoming to Chicago Midway Airport are Frontier ($65), Southwest ($76), and Delta ($109).

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

    When deciding which route to take from Wyoming to Chicago Midway Airport consider Denver Intl - Chicago Midway, Salt Lake City - Chicago Midway or Jackson Hole - Chicago Midway as they are the most popular.

  • Can I find deals for flights from Wyoming to Midway that include hotel bookings?

    Yes. In addition to deals on Wyoming to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wyoming to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wyoming to Midway.

  • Can I find deals for business class flights from Wyoming to Midway?

    Yes. Cheapflights offers flight deals from Wyoming to Midway 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 Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Wyoming to Chicago Midway Airport (average of $160). Flying from Wyoming to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

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Alternative routes for Wyoming to Midway

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