$94 Cheap Flights from Indianapolis (IND) to Chicago (MDW)

View $94 flight on Fri, Oct 31, 2025Opens in a new window

Popular airlines from Indianapolis Intl. Airport (IND) to Chicago Midway Airport (MDW)

Cheap Flights from Indianapolis to Chicago (IND-MDW)

Prices were available within the past 7 days and start at $94 for one-way flights and $197 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Nov 24 - Thu, Nov 27
IND
Indianapolis
MDW
Chicago
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Nov 24 from Indianapolis to Chicago, returning Thu, Nov 27, priced at $197 found 4 days ago
Delta
Wed, Dec 31 - Sat, Jan 17
IND
Indianapolis
MDW
Chicago
$207 Roundtrip, found 6 hours ago
$207
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Dec 31 from Indianapolis to Chicago, returning Sat, Jan 17, priced at $207 found 6 hours ago
Southwest Airlines
Wed, Nov 26 - Thu, Nov 27
IND
Indianapolis
MDW
Chicago
$212 Roundtrip, found 1 day ago
$212
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Nov 26 from Indianapolis to Chicago, returning Thu, Nov 27, priced at $212 found 1 day ago
Delta
Thu, Nov 27 - Tue, Dec 9
IND
Indianapolis
MDW
Chicago
$222 Roundtrip, found 3 days ago
$222
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Nov 27 from Indianapolis to Chicago, returning Tue, Dec 9, priced at $222 found 3 days ago
Southwest Airlines
Sat, Jan 17 - Mon, Jan 19
IND
Indianapolis
MDW
Chicago
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Indianapolis to Chicago, returning Mon, Jan 19, priced at $222 found 2 days ago
Southwest Airlines
Wed, Dec 31 - Thu, Jan 1
IND
Indianapolis
MDW
Chicago
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Dec 31 from Indianapolis to Chicago, returning Thu, Jan 1, priced at $227 found 1 day ago
Southwest Airlines
Fri, Oct 31 - Tue, Nov 11
IND
Indianapolis
MDW
Chicago
$228 Roundtrip, found 3 days ago
$228
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Oct 31 from Indianapolis to Chicago, returning Tue, Nov 11, priced at $228 found 3 days ago
Delta
Tue, Jan 6 - Sat, Jan 17
IND
Indianapolis
MDW
Chicago
$232 Roundtrip, found 3 hours ago
$232
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Jan 6 from Indianapolis to Chicago, returning Sat, Jan 17, priced at $232 found 3 hours ago
Southwest Airlines
Tue, Nov 18 - Thu, Nov 20
IND
Indianapolis
MDW
Chicago
$233 Roundtrip, found 3 days ago
$233
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Indianapolis to Chicago, returning Thu, Nov 20, priced at $233 found 3 days ago
Southwest Airlines
Tue, Nov 18 - Thu, Nov 20
IND
Indianapolis
MDW
Chicago
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Indianapolis to Chicago, returning Thu, Nov 20, priced at $237 found 3 days ago

Find the cheapest month to fly from Indianapolis (IND) to Chicago (MDW)

August is typically the cheapest month to fly

From $127 - $320 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $315
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $315

Frequently asked questions

How much does a flight from Indianapolis Intl. Airport (IND) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $94 or cheap return flight from $197 from Indianapolis Intl. Airport (IND) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Indianapolis Intl. Airport (IND) to Midway Intl. Airport (MDW)?
November is the least expensive month to fly from IND to MDW. Planning your trip for the off-season is often the key to finding a great deal.
What is the cheapest airline that flies from Indianapolis Intl. Airport (IND) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from IND to MDW. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Indianapolis Intl. Airport (IND) to Midway Intl. Airport (MDW)?
There aren't any daily direct flights from Indianapolis Intl. Airport (IND) to Midway Intl. Airport (MDW). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from IND to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Indianapolis Intl. Airport (IND) to Midway Intl. Airport (MDW)?
To land at Midway Intl. Airport (MDW) on time, select a flight that leaves Indianapolis Intl. Airport (IND) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Indianapolis Intl. Airport (IND)?
If you're traveling on a direct flight from Indianapolis Intl. Airport (IND) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Indianapolis Intl. Airport (IND) to Midway Intl. Airport (MDW) last-minute?
Holding off until right before your break to book a flight from IND to MDW often results in higher prices. Although you may find some last-minute deals, there's no guarantee. Keep your travel plans flexible for the best chance of snagging a bargain.
Is it cheaper to book an IND to MDW flight and hotel package?
Opting for an IND to MDW flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Select from our wide range of accommodations and then add car rentals, activities and flights to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Indianapolis Intl. Airport (IND) to Midway Intl. Airport (MDW)?
In most cases, you can cancel or modify your IND to MDW flight. However, additional charges may apply, especially if your booking was made over 24 hours ago. Double-check your itinerary for the airline's rules and fees on flight changes, or if you want further information, head to our Customer Service portal.

Travel information

0
Origin airport
Indianapolis Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$197
Distance
161 mi

Book with confidence

Indianapolis to Chicago Flights

The cheapest times to fly from Indianapolis to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Indianapolis to Chicago are during the month of November. You can find some of the cheapest flights from Indianapolis to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Indianapolis to Chicago

Sunday is one of the best days to book for cheap flights from Indianapolis to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Indianapolis to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Indianapolis to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $94 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Indianapolis to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Indianapolis to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Indianapolis to Chicago Flights

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*Available to One Key members.