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$49+ Cheap flights from Indiana 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
IND — MDW
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheap flight deals from Indiana to Midway

Keep the following information in mind while searching for Indiana to Midway flight deals. Data was last updated septiembre 17, 2025.

Round-trip from

$107
(Southwest)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

August

Average price

$257

Good round-trip deal

$260 or less

Good one-way deal

$157 or less
From Indiana to Chicago Midway
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One-way flight from Indiana to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 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 Indiana to Chicago Midway.
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Price to beat on a one-way flight from Indiana to Chicago Midway.
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Find flight deals from Indiana to Midway

Cheapest flights from Indiana to Midway
Explore the most affordable flight options available from Indiana to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 17, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/43:20 pmSDF - MDW
1 stop6h 45mSouthwest
jue. 11/67:15 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 9/15$107
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/184:25 pmSDF - MDW
Nonstop1h 15mSouthwest
mar. 10/2112:30 pmMDW - SDF
1 stop8h 10mSouthwest
Deal found 9/15$113
This Southwest deal was found by Cheapflights users on 9/16. 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.
mar. 10/143:50 pmSDF - MDW
1 stop6h 00mSouthwest
mié. 10/155:15 amMDW - SDF
1 stop8h 50mSouthwest
Deal found 9/16$122
This Southwest deal was found by Cheapflights users on 9/16. 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.
mar. 10/281:00 pmSDF - MDW
2 stops5h 05mSouthwest
jue. 10/304:35 pmMDW - SDF
2 stops6h 35mSouthwest
Deal found 9/16$127
This Southwest deal was found by Cheapflights users on 9/17. 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.
mié. 10/151:00 pmSDF - MDW
2 stops5h 05mSouthwest
mié. 10/226:10 amMDW - SDF
1 stop9h 10mSouthwest
Deal found 9/17$128
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/810:45 amSDF - MDW
2 stops9h 10mSouthwest
mié. 11/128:25 amMDW - SDF
2 stops7h 45mSouthwest
Deal found 9/15$133
This Southwest deal was found by Cheapflights users on 9/16. 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.
mar. 10/146:55 pmSDF - MDW
Nonstop1h 15mSouthwest
vie. 10/179:25 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 9/16$134
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/208:15 pmSDF - MDW
Nonstop1h 15mSouthwest
vie. 10/244:35 pmMDW - SDF
2 stops6h 35mSouthwest
Deal found 9/14$149
This Southwest deal was found by Cheapflights users on 9/16. 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.
vie. 11/74:45 pmSDF - MDW
1 stop7h 15mSouthwest
sáb. 11/88:25 amMDW - SDF
2 stops6h 45mSouthwest
Deal found 9/16$159
This Frontier deal was found by Cheapflights users on 9/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/203:34 pmIND - MDW
1 stop8h 46mFrontier
vie. 11/1412:30 pmMDW - IND
1 stop6h 14mFrontier
Deal found 9/16$163
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/3010:00 pmIND - MDW
1 stop11h 32mFrontier
sáb. 11/111:36 amMDW - IND
1 stop8h 05mFrontier
Deal found 9/15$165
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/243:34 pmIND - MDW
1 stop8h 46mFrontier
dom. 10/269:26 pmMDW - IND
1 stop12h 11mFrontier
Deal found 9/16$167

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indiana 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 septiembre 17, 2025.
Use the filters below to find and compare flights from Indiana to Chicago Midway Airport that are best for you.

Fly from

Indiana

Fly to

Midway

Route

Depart

Return

Price

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

lun. 10/20

8:15 pm-8:30 pm

Nonstop1h 15m

Chicago Midway

vie. 10/24

4:35 pm-12:10 am

2 stops6h 35m

$149

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

sáb. 10/11

4:25 pm-4:40 pm

Nonstop1h 15m

Chicago Midway

lun. 10/13

9:25 pm-11:40 pm

Nonstop1h 15m

$164

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mar. 11/11

6:00 am-9:52 am

1 stop4h 52m

Chicago Midway

mar. 11/11

5:34 pm-12:06 am

1 stop5h 32m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

sáb. 10/18

3:00 pm-6:25 pm

1 stop4h 25m

Chicago Midway

mar. 10/21

5:04 pm-12:01 am

1 stop5h 57m

$177

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

vie. 9/26

6:05 am-12:44 pm

1 stop7h 39m

Chicago Midway

dom. 9/28

6:20 am-5:38 pm

1 stop10h 18m

$187

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

mié. 11/12

6:00 am-12:34 pm

2 stops7h 34m

Chicago Midway

sáb. 11/15

1:14 pm-11:57 pm

2 stops9h 43m

$187

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

sáb. 10/25

8:00 am-10:47 pm

2 stops15h 47m

Chicago Midway

dom. 10/26

11:57 am-12:42 am

1 stop11h 45m

$192

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

vie. 10/3

12:06 pm-4:00 pm

1 stop4h 54m

Chicago Midway

lun. 10/6

8:19 am-5:10 pm

1 stop7h 51m

$195

Fort WayneChicago

FWA - MDW

FWAMDW

Fort Wayne

jue. 10/30

2:09 pm-6:25 pm

1 stop5h 16m

Chicago Midway

mar. 11/4

9:35 am-1:29 pm

1 stop2h 54m

$199

Fort WayneChicago

FWA - MDW

FWAMDW

Fort Wayne

sáb. 2/28

8:25 am-12:35 pm

1 stop5h 10m

Chicago Midway

mar. 3/3

9:30 am-1:34 pm

1 stop3h 04m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
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Best time to book a flight from Indiana to Midway

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

What is the cheapest time of day to fly from IN to MDW?

Find hourly flight availability from Indiana to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 17, 2025.

When flying from Indiana to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Indiana to Midway. 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 Indiana to Chicago Midway Airport?

    A quick flight from Indiana to Chicago Midway Airport can take about 1h 15m. Southwest provides one of the quickest options available for as low as $149. Indiana and Chicago Midway Airport are separated by a distance of 271 mi. This flight may include one or multiple stops.

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

    While some choose either Indianapolis - Chicago Midway or Dayton - Chicago Midway, Cincinnati Cinci./N. Kentucky - Chicago Midway is the most popular route from Indiana to Chicago Midway Airport.

  • What are the cheapest flights from Indiana to Chicago Midway Airport?

    The cheapest flight price from Indiana to Chicago Midway Airport is $94. On average you can expect to pay $258. The most popular route, (Cincinnati Cinci./N. Kentucky - Chicago Midway), can usually be booked for $153.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Indiana 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 Indiana to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Indiana to Chicago Midway Airport (average of $160). Flying from Indiana 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Indiana to Midway

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