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$50+ Cheap flights from Indianapolis (IND) 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
IND — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Indianapolis to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Indianapolis (IND) to Midway (MDW). 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 September 11, 2025.

Round-trip from

$99
(Southwest)

One-way from

$50
(Southwest)

Popular in

March

Cheapest in

August

Average price

$241

Good round-trip deal

$256 or less

Good one-way deal

$138 or less
From Indianapolis to Chicago Midway
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One-way flight from Indianapolis 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 Indianapolis to Chicago Midway.
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Price to beat on a one-way flight from Indianapolis to Chicago Midway.
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Find flight deals from Indianapolis to Midway

Cheapest flights from Indianapolis to Midway
Explore the most affordable flight options available from Indianapolis to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 11/57:10 amIND - MDW
Nonstop1h 15mSouthwest
Sat 11/87:45 pmMDW - IND
Nonstop1h 00mSouthwest
Deal found 9/11$99
This Southwest deal was found by Cheapflights users on 9/11. 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 11/66:50 amIND - MDW
Nonstop1h 10mSouthwest
Sun 11/910:15 amMDW - IND
Nonstop1h 10mSouthwest
Deal found 9/11$131
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Thu 10/233:33 pmIND - MDW
1 stop8h 47mFrontier
Mon 10/275:10 amMDW - IND
1 stop7h 41mFrontier
Deal found 9/10$157
This Southwest deal was found by Cheapflights users on 9/11. 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 10/76:25 amIND - MDW
Nonstop1h 05mSouthwest
Thu 10/99:45 amMDW - IND
Nonstop1h 00mSouthwest
Deal found 9/11$158
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Thu 10/233:33 pmIND - MDW
1 stop8h 47mMultiple Airlines
Mon 10/275:10 amMDW - IND
2 stops37h 33mMultiple Airlines
Deal found 9/10$165
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
Mon 11/311:24 amIND - MDW
1 stop11h 47mMultiple Airlines
Tue 12/168:00 amMDW - IND
2 stops12h 00mMultiple Airlines
Deal found 9/10$168
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Sun 10/56:40 pmIND - MDW
1 stop19h 31mMultiple Airlines
Tue 10/75:56 pmMDW - IND
1 stop22h 11mMultiple Airlines
Deal found 9/11$173

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indianapolis 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 September 11, 2025.
Use the filters below to find and compare flights from Indianapolis to Chicago Midway Airport that are best for you.

Fly from

Indianapolis

Fly to

Midway

Route

Depart

Return

Price

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 11/5

5:00 pm-5:10 pm

Nonstop1h 10m

Chicago Midway

Sat 11/8

9:45 am-11:50 am

Nonstop1h 05m

$99

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 10/30

6:30 am-8:40 am

1 stop3h 10m

Chicago Midway

Wed 12/17

6:40 pm-12:12 am

1 stop4h 32m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Fri 10/31

6:30 am-8:40 am

1 stop3h 10m

Chicago Midway

Thu 12/18

10:49 am-5:37 pm

1 stop5h 48m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 10/30

6:30 am-8:40 am

1 stop3h 10m

Chicago Midway

Mon 12/15

5:32 pm-12:27 am

1 stop5h 55m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 11/5

4:48 pm-10:14 pm

1 stop6h 26m

Chicago Midway

Thu 12/18

1:14 pm-7:04 pm

1 stop4h 50m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Fri 10/31

6:30 am-8:40 am

1 stop3h 10m

Chicago Midway

Sun 12/14

6:40 pm-12:12 am

1 stop4h 32m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 11/5

4:48 pm-10:14 pm

1 stop6h 26m

Chicago Midway

Wed 12/17

1:14 pm-7:04 pm

1 stop4h 50m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 10/30

6:30 am-8:40 am

1 stop3h 10m

Chicago Midway

Tue 12/16

1:50 pm-7:02 pm

1 stop4h 12m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 11/5

4:48 pm-10:14 pm

1 stop6h 26m

Chicago Midway

Sun 12/14

6:40 pm-12:12 am

1 stop4h 32m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 12/6

4:35 pm-4:45 pm

Nonstop1h 10m

$50

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 16 results
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Best time to book a flight from Indianapolis to Midway

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

What is the cheapest month to book a flight from Indianapolis to Chicago Midway Airport?

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

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

Find hourly flight availability from Indianapolis 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 September 11, 2025.

It’s typically best to fly out from Indianapolis to Chicago Midway Airport at noon. Doing so could potentially save you 9% on the flight price compared to flying in the morning, which is usually more expensive.

Related info for your journey

Find useful and relevant information for your journey from Indianapolis to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Indianapolis to Chicago Midway?

    Indianapolis (IND), located 8.3 mi from the city center, is the airport you fly out of when you book flights from Indianapolis to Chicago Midway. 0 airlines have flights from Indianapolis to Chicago Midway on a regular basis. Booking flights from Indianapolis to Chicago Midway should not be difficult; the airport handles an average of 1 outbound flight to Chicago Midway per day.

  • How long is the flight from Indianapolis to Chicago Midway Airport?

    For as low as $99, Southwest can have you in Chicago Midway Airport from Indianapolis in 1h 10m. The distance from Indianapolis to Chicago Midway Airport is about 162 mi. This flight may include one or multiple stops.

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

    Looking for the cheapest flight from Indianapolis to Chicago Midway Airport? While on average our users pay $251, our data indicates the cheapest price to be $94. The most popular route (Indianapolis - Chicago Midway), is priced around $99.

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

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

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

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

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

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

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