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$68+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
IND — CHI
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/207:41 pm
IND
-
ORD
1 stop16h 05m
Frontier
Wed 2/256:02 pm
ORD
-
IND
1 stop23h 29m
Frontier
Deal found 1/21$130
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/168:02 pm
IND
-
ORD
1 stop15h 28m
Frontier
Wed 2/186:02 pm
ORD
-
IND
1 stop23h 29m
Frontier
Deal found 1/21$152
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/912:38 pm
IND
-
ORD
1 stop11h 08m
Frontier
Wed 2/116:02 pm
ORD
-
IND
1 stop23h 29m
Frontier
Deal found 1/21$154
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/212:38 pm
IND
-
MDW
1 stop10h 41m
Frontier
Wed 2/41:20 pm
MDW
-
IND
1 stop21h 23m
Frontier
Deal found 1/21$154
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/177:15 am
IND
-
ORD
Nonstop1h 18m
United Airlines
Tue 2/243:45 pm
ORD
-
IND
Nonstop1h 08m
United Airlines
Deal found 1/20$157
This Southwest deal was found by Cheapflights users on 1/20. 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 3/34:25 pm
IND
-
MDW
Nonstop1h 00m
Southwest
Wed 3/410:00 am
MDW
-
IND
Nonstop1h 10m
Southwest
Deal found 1/20$157
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 1/2912:38 pm
IND
-
MDW
1 stop10h 41m
Frontier
Sun 2/16:20 am
MDW
-
IND
1 stop28h 23m
Frontier
Deal found 1/21$158
This Expedia deal was found by Cheapflights users on 1/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/212:38 pm
IND
-
ORD
1 stop11h 08m
Frontier
Thu 2/55:40 am
ORD
-
IND
1 stop5h 03m
Frontier
Deal found 1/19$160
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/197:27 pm
IND
-
ORD
1 stop28h 12m
Frontier
Thu 2/264:16 pm
ORD
-
IND
1 stop26h 31m
Frontier
Deal found 1/20$162
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/106:18 pm
IND
-
ORD
Nonstop1h 37m
American Airlines
Thu 2/2610:11 pm
ORD
-
IND
Nonstop1h 07m
American Airlines
Deal found 1/20$164
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Tue 2/178:18 pm
IND
-
ORD
1 stop16h 04m
Spirit Airlines
Tue 2/245:58 pm
ORD
-
IND
1 stop28h 27m
Spirit Airlines
Deal found 1/20$165
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/255:45 am
IND
-
ORD
1 stop14h 26m
Spirit Airlines
Fri 2/275:58 pm
ORD
-
IND
1 stop28h 27m
Spirit Airlines
Deal found 1/20$168

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$130
(Kiwi.com)

One-way from

$68
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$257

Good round-trip deal

$363 or less

Good one-way deal

$219 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. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 21, 2026.
Use the filters below to find and compare flights from Indianapolis to Chicago that are best for you.

Fly from

Indianapolis

Fly to

Chicago

Route

Depart

Return

Price

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Tue 2/17

7:15 am-7:33 am

Nonstop1h 18m

Chicago O'Hare Intl

Tue 2/24

3:45 pm-5:53 pm

Nonstop1h 08m

$157

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 1/29

12:38 pm-10:19 pm

1 stop10h 41m

Chicago Midway

Sun 2/1

6:20 am-11:43 am

1 stop28h 23m

$158

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Thu 2/19

7:27 pm-10:39 pm

1 stop28h 12m

Chicago O'Hare Intl

Thu 2/26

4:16 pm-7:47 pm

1 stop26h 31m

$162

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Wed 3/4

7:00 am-7:26 am

Nonstop1h 26m

Chicago O'Hare Intl

Thu 3/5

2:55 pm-4:58 pm

Nonstop1h 03m

$164

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Thu 2/19

6:10 pm-6:28 pm

Nonstop1h 18m

Chicago O'Hare Intl

Thu 2/26

12:45 pm-2:58 pm

Nonstop1h 13m

$171

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Sat 2/21

1:57 pm-2:14 pm

Nonstop1h 17m

Chicago O'Hare Intl

Sat 2/28

1:10 pm-3:17 pm

Nonstop1h 07m

$171

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 2/18

11:25 am-2:55 pm

1 stop4h 30m

Chicago Midway

Sat 2/21

11:20 am-1:30 pm

Nonstop1h 10m

$174

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Mon 2/16

9:55 am-1:50 pm

1 stop4h 55m

Chicago Midway

Wed 2/18

10:00 am-12:10 pm

Nonstop1h 10m

$174

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 2/19

5:05 am-9:00 am

1 stop4h 55m

Chicago Midway

Thu 2/26

8:05 am-10:15 am

Nonstop1h 10m

$181

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 3/3

10:30 am-4:40 pm

1 stop7h 10m

Chicago Midway

Wed 3/4

9:55 am-7:55 pm

2 stops9h 00m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 44 results
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Expedia the most. Expedia 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

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

Currently, February is the cheapest month in which you can book a flight from Indianapolis to Chicago (average of $127). Flying from Indianapolis to Chicago in June is currently the most expensive (average of $179). 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 January 21, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 54% 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 January 17, 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. Saturday 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 January 21, 2026.

The most flights from IND to CHI are scheduled on a Monday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (40 on average).

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 January 21, 2026.
Get a feel of what it's like to fly with Southwest, United Airlines, and American 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
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,191 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,174 reviews
Southwest
8.0
Very good
4,266 reviews

Crew

8.6

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 54 daily outbound flights to Chicago from 3 different airlines.

  • How long is the flight from Indianapolis to Chicago?

    United Airlines, Frontier, and American Airlines can get you from Indianapolis to Chicago in just under 1h 18m. Your travel time can differ by up to 9h 23m. Airlines will cover a distance of 177 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 $137 on this airline. Additional options worth looking into are United Airlines and Southwest, starting at $178 and $192 round-trip. American Airlines is priced at 50% lower than the current average price of a flight leaving 3 months from now.

  • 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: Envoy Air (100%), Royal Jordanian (80%), Japan Airlines (78%).

  • What are the cheapest flights from Indianapolis to Chicago?

    Looking at all options, your cheapest flight can be booked for $127. While the most popular route (Indianapolis - Chicago O'Hare Intl) can be booked for $157 on average, our data indicates $853 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, February is the cheapest month in which you can book a flight from Indianapolis to Chicago (average of $127). Flying from Indianapolis to Chicago in June is currently the most expensive (average of $179). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Indianapolis to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$137Average$247FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$178Average$286FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$192Average$337FlexibilityNo cancel feeOn-time63%

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