$101 Cheap Flights from Indianapolis (IND) to Chicago (MDW)

View $101 flight on Thu, Apr 9, 2026Opens in a new window

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

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Cheap Flights from Indianapolis to Chicago (IND-MDW)

Prices were available within the past 7 days and start at $101 for one-way flights and $97 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Apr 21 - Wed, Apr 22
IND
Indianapolis
MDW
Chicago
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Apr 21 from Indianapolis to Chicago, returning Wed, Apr 22, priced at $97 found 2 days ago
Delta
Tue, Apr 21 - Wed, Apr 22
IND
Indianapolis
MDW
Chicago
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 21 from Indianapolis to Chicago, returning Wed, Apr 22, priced at $127 found 2 days ago
Delta
Tue, Apr 21 - Wed, Apr 22
IND
Indianapolis
MDW
Chicago
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 21 from Indianapolis to Chicago, returning Wed, Apr 22, priced at $157 found 2 days ago
Delta
Tue, Apr 21 - Wed, Apr 22
IND
Indianapolis
MDW
Chicago
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Apr 21 from Indianapolis to Chicago, returning Wed, Apr 22, priced at $157 found 2 days ago
Southwest Airlines
Thu, Apr 9 - Tue, Apr 14
IND
Indianapolis
MDW
Chicago
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Apr 9 from Indianapolis to Chicago, returning Tue, Apr 14, priced at $164 found 2 days ago
Southwest Airlines
Thu, Apr 9 - Tue, Apr 14
IND
Indianapolis
MDW
Chicago
$174 Roundtrip, found 2 days ago
$174
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Apr 9 from Indianapolis to Chicago, returning Tue, Apr 14, priced at $174 found 2 days ago
Delta
Sat, May 2 - Sat, May 9
IND
Indianapolis
MDW
Chicago
$177 Roundtrip, found 5 days ago
$177
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, May 2 from Indianapolis to Chicago, returning Sat, May 9, priced at $177 found 5 days ago
Southwest Airlines
Tue, Mar 31 - Sat, Apr 11
IND
Indianapolis
MDW
Chicago
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Mar 31 from Indianapolis to Chicago, returning Sat, Apr 11, priced at $179 found 2 days ago
Southwest Airlines
Thu, Apr 9 - Tue, Apr 14
IND
Indianapolis
MDW
Chicago
$179 Roundtrip, found 2 days ago
$179
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Apr 9 from Indianapolis to Chicago, returning Tue, Apr 14, priced at $179 found 2 days ago
Southwest Airlines
Tue, Mar 31 - Sat, Apr 11
IND
Indianapolis
MDW
Chicago
$184 Roundtrip, found 2 days ago
$184
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Mar 31 from Indianapolis to Chicago, returning Sat, Apr 11, priced at $184 found 2 days ago

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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. Average driving time to city center is 23 minutes. Flights from $419
ORD
O'Hare Intl.
Average driving time to city center23 min
Flights from $419

Frequently asked questions

How much does a flight from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from $101 and cheap return flights from $97 Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) with Expedia. One-way flights usually range from $116 to $357, and return flights typically cost between $274 and $622. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) ticket fares go up or down.*Typical price ranges based on flights available on Expedia in the last year. Prices include multi-airline options.
What is the cheapest month to fly from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest month to fly from IND to MDW is April when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you're able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter IND to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
Southwest Airlines is one of the cheapest airlines offering nonstop flights from Indianapolis (IND) to Chicago (MDW), with round-trip tickets starting from around $220. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.*Prices based on flights available on Expedia in the last year.
How do I find cheap flights from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best airline to fly with from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best airline to fly with from Indianapolis, IN (IND) to Chicago, IL (MDW) will differ from traveler to traveler. If you like to fly early, WN offers early morning flights. If price is the most important factor, WN typically offers the lowest fares. WN offers the most daily flights from IND to MDW, which is great if flexibility is what you value most. The best carrier for this journey could also be the one you have a loyalty membership with, as flying with that airline or another airline within the same alliance could help you collect points or enjoy lounge access.
What is the best time to fly from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can find approximately 2 nonstop flights per day from Indianapolis Intl. (IND) to Midway Intl. (MDW). For more options, look at flights that include layovers.
What is the earliest flight from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Indianapolis International Airport (IND) to Chicago Midway International Airport (MDW) typically departs at around 5:00 AM, operated by Southwest Airlines. An early departure like this allows you to make the most of your day in Chicago. This service operates seasonally in April and May. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What are the most popular departure times for flights from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Indianapolis (IND) to Chicago (MDW) are in the early morning, from 6am to 9am. About 31% of passengers prefer this time window. Delta Airlines and Southwest Airlines both offer flights during this period. Many travelers choose this timing to start their day early and make the most of their time in Chicago.
How long does it take to fly from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
Direct flights from IND to MDW usually take about 1 hour, traveling roughly 162 miles. If you opt for a connecting flight, expect to add around 6 hours to your journey. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
First class seats are offered on the IND to MDW route with Delta Air Lines.
How do I earn miles on a Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago from Indianapolis Intl. (IND)?
When traveling from Indianapolis Intl. (IND) to Chicago, you can fly into Midway Intl. (MDW) and O'Hare Intl. (ORD). Some flights may connect through major hubs like Baltimore Washington Intl. Thurgood Marshall (BWI), Washington Dulles Intl. (IAD), Denver Intl. (DEN) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) Chicago Vacation Packages is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals 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, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Indianapolis, IN (IND-Indianapolis Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

0
Origin airport
Indianapolis Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$97
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 April. 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 2026. You can also book with separate airlines for your outbound and return journeys, from $101 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

*Flight schedules are subject to change.

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