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Midway

$78+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
JAC — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$153
(Priceline)

One-way from

$78
(Flightnetwork)

Popular in

March

Cheapest in

September

Average price

$526
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. 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 ($20 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Priceline deal was found by Cheapflights users on 7/2. 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.
Sat 8/2312:54 amDEN - MDW
1 stop8h 14mFrontier
Sat 8/306:10 amMDW - DEN
1 stop9h 08mFrontier
Deal found 7/2$153
This Southwest deal was found by Cheapflights users on 7/2. 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.
Thu 8/288:45 pmDEN - MDW
Nonstop2h 20mSouthwest
Sat 8/307:25 pmMDW - DEN
Nonstop2h 40mSouthwest
Deal found 7/2$157
This Frontier deal was found by Cheapflights users on 7/2. 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.
Fri 8/223:45 pmSLC - MDW
1 stop7h 39mFrontier
Mon 8/256:31 pmMDW - SLC
1 stop6h 48mFrontier
Deal found 7/2$203
This Southwest deal was found by Cheapflights users on 7/3. 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.
Thu 8/75:00 amSLC - MDW
Nonstop3h 00mSouthwest
Mon 8/117:55 amMDW - SLC
Nonstop3h 20mSouthwest
Deal found 7/3$257
This Delta deal was found by Cheapflights users on 7/2. 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 7/96:53 pmJAC - MDW
2 stops12h 51mDelta
Sat 7/121:46 pmMDW - JAC
1 stop6h 55mDelta
Deal found 7/2$439

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 July 3, 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 8/23

12:54 am-10:08 am

1 stop8h 14m

Chicago Midway

Sat 8/30

6:10 am-2:18 pm

1 stop9h 08m

$153

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 8/28

8:45 pm-12:05 am

Nonstop2h 20m

Chicago Midway

Tue 9/2

8:50 pm-10:25 pm

Nonstop2h 35m

$157

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Fri 8/22

3:45 pm-12:24 am

1 stop7h 39m

Chicago Midway

Mon 8/25

6:31 pm-12:19 am

1 stop6h 48m

$203

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Thu 8/7

5:00 am-9:00 am

Nonstop3h 00m

Chicago Midway

Mon 8/11

7:55 am-10:15 am

Nonstop3h 20m

$257

JacksonChicago

JAC - MDW

JACMDW

Jackson Hole

Wed 7/9

6:53 pm-8:44 am

2 stops12h 51m

Chicago Midway

Sat 7/12

1:46 pm-7:41 pm

1 stop6h 55m

$439

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Thu 8/14

5:26 pm-8:54 pm

Nonstop2h 28m

$78

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Wed 8/13

2:50 pm-6:10 pm

Nonstop2h 20m

$79

DenverChicago

DEN - MDW

DENMDW

Denver Intl

Mon 9/29

12:59 am-9:40 am

1 stop7h 41m

$109

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Thu 10/16

12:48 pm-10:01 pm

1 stop8h 13m

$118

Salt Lake CityChicago

SLC - MDW

SLCMDW

Salt Lake City

Tue 8/19

8:10 am-12:15 pm

Nonstop3h 05m

$129

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 12 results
1
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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
No data available for this route at this time. Please check back soon.

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 July 3, 2025.
See what other customers who have flown with Southwest, Delta, and Frontier from Wyoming to Chicago Midway Airport have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 ($78), Southwest ($79), 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Wyoming to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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