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$79 Cheap Flights from Indianapolis (IND) to Chicago (MDW)

View $79 flight on Sat, Sep 5, 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 $79 for one-way flights and $157 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Sep 5 - Sun, Sep 6
IND
Indianapolis
MDW
Chicago
$157 Roundtrip, found 6 hours ago
$157
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Indianapolis to Chicago, returning Sun, Sep 6, priced at $157 found 6 hours ago
Southwest Airlines
Sat, Sep 5 - Sun, Sep 6
IND
Indianapolis
MDW
Chicago
$167 Roundtrip, found 6 hours ago
$167
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Indianapolis to Chicago, returning Sun, Sep 6, priced at $167 found 6 hours ago
Southwest Airlines
Sat, Sep 5 - Sun, Sep 6
IND
Indianapolis
MDW
Chicago
$192 Roundtrip, found 6 hours ago
$192
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Indianapolis to Chicago, returning Sun, Sep 6, priced at $192 found 6 hours ago
Southwest Airlines
Sat, Sep 5 - Sun, Sep 6
IND
Indianapolis
MDW
Chicago
$197 Roundtrip, found 6 hours ago
$197
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Indianapolis to Chicago, returning Sun, Sep 6, priced at $197 found 6 hours ago
Delta
Sat, Sep 5 - Sun, Sep 6
IND
Indianapolis
MDW
Chicago
$202 Roundtrip, found 6 hours ago
$202
Roundtrip
found 6 hours ago
Select Delta flight, departing Sat, Sep 5 from Indianapolis to Chicago, returning Sun, Sep 6, priced at $202 found 6 hours ago
Southwest Airlines
Wed, Sep 2 - Sat, Sep 5
IND
Indianapolis
MDW
Chicago
$207 Roundtrip, found 11 hours ago
$207
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Indianapolis to Chicago, returning Sat, Sep 5, priced at $207 found 11 hours ago
Southwest Airlines
Wed, Sep 2 - Sat, Sep 5
IND
Indianapolis
MDW
Chicago
$212 Roundtrip, found 11 hours ago
$212
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Indianapolis to Chicago, returning Sat, Sep 5, priced at $212 found 11 hours ago
Delta
Wed, Sep 2 - Sat, Sep 5
IND
Indianapolis
MDW
Chicago
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Sep 2 from Indianapolis to Chicago, returning Sat, Sep 5, priced at $217 found 11 hours ago
Southwest Airlines
Fri, Aug 28 - Sat, Sep 5
IND
Indianapolis
MDW
Chicago
$220 Roundtrip, found 9 hours ago
$220
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Fri, Aug 28 from Indianapolis to Chicago, returning Sat, Sep 5, priced at $220 found 9 hours ago
Southwest Airlines
Wed, Sep 2 - Sat, Sep 5
IND
Indianapolis
MDW
Chicago
$222 Roundtrip, found 11 hours ago
$222
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Indianapolis to Chicago, returning Sat, Sep 5, priced at $222 found 11 hours ago

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 $449
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $449

What you need to know for your flight from Indianapolis Intl. to Midway Intl.

Indianapolis (IND) to Chicago (MDW) at a glance

Travel conveniently between Indianapolis (IND) and Chicago (MDW) on this popular domestic short-haul route. Explore various airlines offering flights from Indianapolis to Chicago, allowing you to compare both full-service and low-cost options. This way, you can choose the itinerary that aligns with your budget and schedule as you prepare to experience Chicago's renowned attractions and neighborhoods. Check out the essential details for flights from Indianapolis International Airport to Midway International Airport.

  • Fastest flight duration: around 1 hour non-stop
  • Route distance: roughly 150 miles (240 km)
  • Flights per week: around 8 departures on average
  • Typical fares (one-way): economy tickets often range from $90–$335, depending on seasonality and how far ahead you book

Flights from Indianapolis International Airport (IND) to Midway International Airport (MDW)

Based on recent traveler bookings, here are the top airlines favored for flights from Indianapolis to Chicago, featuring both non-stop and one-stop options. A common layover occurs at Detroit Metropolitan Wayne County Airport (DTW), where the typical wait is around 50 minutes. This allows you to easily compare prices, total travel times, and cabin classes to find the ideal itinerary that suits your needs.

  • Southwest Airlines: This budget-friendly airline provides non-stop flights, with one-way ticket prices generally falling between $90 and $335. It dominates the route, making up about 88% of departures, and the total travel duration is just 1 hour.
  • Delta: As a full-service airline, Delta offers one-stop flights with one-way fares usually ranging from $115 to $265. It represents roughly 12% of the departures on this route, featuring an in-flight duration of 2 hours and 30 minutes, leading to a total travel time of approximately 3 hours and 15 minutes, including layover.

Alternative route from Indianapolis (IND) to Chicago (MDW)

  • Indianapolis to Chicago (IND-ORD): O'Hare International Airport (ORD) is located approximately 16 miles from Midway International Airport (MDW). One-way economy ticket prices for this journey generally vary from $80 to $305, influenced by the time of year and when the booking is made. Passengers can typically choose between non-stop and one-stop flights. Major airlines operating this route include United and American Airlines, with first-class service also offered.

How to find the best prices for flights from Indianapolis (IND) to Chicago (MDW)

Getting some of the best deals on flights from Indianapolis to Chicago is all about timing and flexibility. Here are some key tips to help you save:

  1. Best times to book and fly: cheaper fares are usually available when booking at least two months in advance, although most travelers tend to book between two to eight weeks ahead. Afternoon departures, from 12 PM to 6 PM, typically offer lower prices and are also the most popular. Additionally, flying on Tuesday generally provides cheaper options, while Friday remains the busiest travel day.
  2. Set up price alerts: stay updated on price changes by using Expedia's Price Tracker. Receive alerts when fares drop for your selected route.
  3. Bundle and save: bundle your flight and hotel to save on Expedia, or unlock a hotel deal after booking your flight.*
  4. Compare flight options: use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  5. Stay flexible with dates: being open to different travel days can sometimes help you find better prices on flights and hotels.
  6. Think about luggage: nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your allowance before confirming your booking to avoid excess baggage fees at the airport.

*Members only. Savings vary and are not available on all bundles. Select hotels.

Arriving at Midway International Airport from Indianapolis International Airport

Chicago welcomes travelers from Indianapolis with a range of transport options based on price, convenience, and proximity. Here's how to reach Chicago efficiently:

  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Chicago, with private rides that can be arranged in advance.
  • Car rental: Renting a car from Midway International Airport is a great option if you plan to explore and sightsee beyond the city. Browse cheap car rentals at Midway International Airport on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.
  • Public transportation: From Midway International Airport, Midway Station (a metro station) is conveniently located just 0.2 miles away on foot, while Chicago Ashburn Station (a train station) is approximately 4.1 miles away by car. For those looking to travel by sea, Lyons Seaport (a seaport) is situated about 7.2 miles away by car.

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 $79 and cheap return flights from $157 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 September 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
$157
Distance
161 mi

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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 September. 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 $79 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.

*Available to One Key members.

 

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