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$74+ Cheap flights from Indianapolis (IND) to Chicago (CHI)

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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
IND — CHI
Jun 3 — Jun 101
Wed 6/3
Wed 6/10
1 adult, Economy
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Cheap flight deals from Indianapolis to Chicago

Cheapest flights from Indianapolis to Chicago
Explore the most affordable flight options available from Indianapolis to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Wed 5/2712:14 pm
IND
-
ORD
1 stop20h 41m
Frontier
Tue 6/26:55 am
ORD
-
IND
1 stop27h 28m
Frontier
Deal found 5/3$145
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/238:42 pm
IND
-
ORD
Nonstop1h 28m
American Airlines
Wed 6/2410:30 pm
ORD
-
IND
Nonstop1h 22m
American Airlines
Deal found 5/1$157
This Southwest deal was found by Cheapflights users on 5/1. 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 6/236:40 am
IND
-
MDW
Nonstop1h 10m
Southwest
Wed 6/249:20 pm
MDW
-
IND
Nonstop1h 05m
Southwest
Deal found 5/1$157
This American Airlines deal was found by Cheapflights users on 5/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/1612:20 pm
IND
-
ORD
Nonstop1h 28m
American Airlines
Tue 6/231:14 pm
ORD
-
IND
Nonstop1h 12m
American Airlines
Deal found 5/2$159
This Kiwi.com deal was found by Cheapflights users on 5/3. 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.
Fri 7/312:14 pm
IND
-
ORD
1 stop20h 49m
Frontier
Tue 7/211:50 pm
ORD
-
IND
1 stop20h 15m
Frontier
Deal found 5/3$168
This Southwest deal was found by Cheapflights users on 5/2. 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 6/164:50 pm
IND
-
MDW
Nonstop1h 10m
Southwest
Tue 6/237:50 am
MDW
-
IND
2 stops7h 25m
Southwest
Deal found 5/2$172
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Wed 5/2712:14 pm
IND
-
ORD
1 stop8h 27m
Frontier
Thu 5/281:50 pm
ORD
-
IND
1 stop20h 33m
Frontier
Deal found 4/30$174
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/235:30 pm
IND
-
ORD
1 stop4h 01m
Delta
Wed 6/245:22 pm
ORD
-
IND
1 stop5h 48m
Delta
Deal found 5/1$177
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/2212:14 pm
IND
-
ORD
1 stop20h 49m
Frontier
Thu 6/256:55 am
ORD
-
IND
1 stop27h 24m
Frontier
Deal found 5/1$179
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:21 pm
IND
-
ORD
Nonstop1h 24m
American Airlines
Thu 6/41:17 pm
ORD
-
IND
Nonstop1h 12m
American Airlines
Deal found 4/30$189
This Southwest deal was found by Cheapflights users on 5/2. 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.
Sat 5/232:40 pm
IND
-
MDW
Nonstop1h 00m
Southwest
Tue 6/210:00 am
MDW
-
IND
Nonstop1h 05m
Southwest
Deal found 5/2$189
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 7/612:20 pm
IND
-
ORD
1 stop20h 33m
Frontier
Tue 8/117:05 am
ORD
-
IND
1 stop27h 00m
Frontier
Deal found 5/3$192

Find flight deals from Indianapolis to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Indianapolis (IND) to Chicago (CHI). 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 May 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$145
(Kiwi.com)

One-way from

$74
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$236

Good round-trip deal

$372 or less

Good one-way deal

$193 or less
Provider with most accurate pricing for Indianapolis-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Indianapolis-Chicago (CHI) flights.
Search Deals
From Indianapolis to Chicago (CHI)
Search Deals
One-way flight from Indianapolis to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Indianapolis to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Indianapolis to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indianapolis to Chicago 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 May 4, 2026.
Use the filters below to find and compare flights from Indianapolis to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 6/2

6:40 am-6:35 am

Nonstop0h 55m

Chicago Midway

Tue 6/9

9:20 pm-11:25 pm

Nonstop1h 05m

$157

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Tue 6/2

4:49 pm-9:20 pm

1 stop5h 31m

Chicago O'Hare Intl

Tue 6/9

3:55 pm-12:17 am

1 stop7h 22m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 5/23

2:40 pm-2:40 pm

Nonstop1h 00m

Chicago Midway

Tue 6/2

10:00 am-12:05 pm

Nonstop1h 05m

$189

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Wed 6/3

3:59 pm-8:14 pm

1 stop5h 15m

Chicago O'Hare Intl

Thu 6/4

7:00 am-1:27 pm

1 stop5h 27m

$209

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 5/28

6:50 am-6:45 am

Nonstop0h 55m

Chicago Midway

Mon 6/1

9:45 pm-11:55 pm

Nonstop1h 10m

$221

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 5/30

6:35 am-6:30 am

Nonstop0h 55m

Chicago Midway

Sat 6/6

8:25 pm-10:30 pm

Nonstop1h 05m

$221

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 5/28

2:25 pm-8:05 pm

2 stops6h 40m

Chicago Midway

Thu 6/4

9:25 pm-11:25 pm

Nonstop1h 00m

$236

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 6/16

6:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

Thu 6/18

10:00 am-12:05 pm

Nonstop1h 05m

$237

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 6/10

6:40 am-6:50 am

Nonstop1h 10m

Chicago Midway

Fri 6/12

10:00 am-12:05 pm

Nonstop1h 05m

$237

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Sat 5/30

10:35 am-12:56 pm

1 stop3h 21m

Chicago O'Hare Intl

Sat 6/6

6:24 am-11:58 am

1 stop4h 34m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 38 resultsSorted by cheapest first
1
2
3
4

Compare providers for flights from Indianapolis to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Indianapolis to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Indianapolis-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Indianapolis-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Indianapolis-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Indianapolis-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Indianapolis-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Indianapolis to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

How far ahead should I book a flight from Indianapolis to Chicago?

Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from Indianapolis to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, August is the cheapest month in which you can book a flight from Indianapolis to Chicago (average of $98). Flying from Indianapolis to Chicago in November is currently the most expensive (average of $212). 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 CHI?

Find hourly flight availability from Indianapolis to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 4, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 37% on flights from Indianapolis to Chicago by exploring options for tickets in the morning.

What is the cheapest day to fly from Indianapolis to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Indianapolis to Chicago. Price data was last updated on May 2, 2026.

Travelers seeking maximum savings on their Indianapolis to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Indianapolis to Chicago

Explore weekly flight availability from Indianapolis to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 4, 2026.

The most flights from IND to CHI are scheduled on a Monday (95 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (71 on average).

How much does it cost to fly round-trip from Indianapolis to Chicago?

The best insider tips for Indianapolis to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Indianapolis to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Barbara Noe Kennedy

Barbara Noe Kennedy

Expert on IND

Award-winning travel journalist Barbara Noe Kennedy writes about destinations around the world—but her heart is in her home state of Virginia, where she’s always researching her next travel story.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 4, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Indianapolis to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,307 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,307 reviews
Southwest
7.9
Good
4,307 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,680 reviews
Southwest
7.9
Good
4,307 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,673 reviews
Southwest
7.9
Good
4,307 reviews

Overall

7.9

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Indianapolis to Chicago. 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?

    Located just 8.3 mi from the city center, Indianapolis is the airport most travelers will use when flying to Chicago from Indianapolis. Booking flights from Indianapolis (IND) to Chicago should be relatively easy as there are 85 daily outbound flights to Chicago from 3 different airlines.

  • How long is the flight from Indianapolis to Chicago?

    Southwest and Delta can get you from Indianapolis to Chicago in just under 55m. Your travel time can differ by up to 4h 36m. Airlines will cover a distance of 162 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Indianapolis to Chicago round-trip?

    Our cheapest airline available from Indianapolis to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $136 on this airline. Additional options worth looking into are United Airlines and Southwest, starting at $157 and $192 round-trip. American Airlines is priced at 51% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Indianapolis to Chicago one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $93. Users have also found prices from $96 and $121 on American Airlines and Southwest, respectively.

  • What are the most reliable airlines from Indianapolis to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Indianapolis to Chicago on time: GoJet (100%), Finnair (80%), Republic Airways (79%).

  • What are the cheapest flights from Indianapolis to Chicago?

    Looking at all options, your cheapest flight can be booked for $146. While the most popular route (Indianapolis - Chicago O'Hare Intl) can be booked for $157 on average, our data indicates $1,035 when flying from Indianapolis to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Indianapolis to Chicago 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?

    Currently, August is the cheapest month in which you can book a flight from Indianapolis to Chicago (average of $98). Flying from Indianapolis to Chicago in November is currently the most expensive (average of $212). 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?

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

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Top 3 airlines flying from Indianapolis to Chicago

Discover the top 3 airlines that operate flights from Indianapolis to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$136Average$240FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$299FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$192Average$337FlexibilityNo cancel feeOn-time63%

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