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$55+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
IND — CHI
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
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Find 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 November 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/26:07 pmIND - ORD
1 stop21h 50mMultiple Airlines
Fri 12/58:36 amORD - IND
1 stop22h 07mMultiple Airlines
Deal found 11/17$175
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/236:39 pmIND - ORD
2 stops16h 39mMultiple Airlines
Sat 1/2412:00 pmORD - IND
1 stop9h 48mMultiple Airlines
Deal found 11/18$192
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/174:53 pmIND - ORD
Nonstop1h 30mAmerican Airlines
Wed 12/2411:25 amORD - IND
Nonstop1h 15mAmerican Airlines
Deal found 11/19$197
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/35:00 amIND - ORD
1 stop8h 56mMultiple Airlines
Sun 12/77:41 pmORD - IND
2 stops22h 09mMultiple Airlines
Deal found 11/18$209
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/36:07 pmIND - MDW
1 stop19h 54mMultiple Airlines
Sun 12/77:44 amMDW - IND
1 stop22h 59mMultiple Airlines
Deal found 11/18$209
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1312:03 pmIND - ORD
1 stop8h 58mMultiple Airlines
Sun 12/143:20 pmORD - IND
1 stop18h 38mMultiple Airlines
Deal found 11/19$212
This Southwest deal was found by Cheapflights users on 11/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:10 amIND - MDW
Nonstop1h 15mSouthwest
Wed 12/246:40 amMDW - IND
1 stop9h 00mSouthwest
Deal found 11/19$213
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/35:00 amIND - ORD
1 stop8h 56mMultiple Airlines
Wed 12/34:01 pmORD - IND
2 stops28h 34mMultiple Airlines
Deal found 11/17$215
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:32 amIND - ORD
1 stop4h 18mDelta
Wed 12/241:35 pmORD - IND
1 stop4h 25mDelta
Deal found 11/19$217
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:32 amIND - MDW
1 stop3h 02mDelta
Wed 12/246:08 pmMDW - IND
1 stop3h 46mDelta
Deal found 11/19$217
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 12/25:00 amIND - ORD
1 stop8h 56mMultiple Airlines
Wed 12/34:01 pmORD - IND
2 stops28h 34mMultiple Airlines
Deal found 11/17$219
This Mytrip deal was found by Cheapflights users on 11/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/25:00 amIND - ORD
1 stop10h 31mSpirit Airlines
Wed 12/33:53 pmORD - IND
1 stop14h 50mSpirit Airlines
Deal found 11/17$221

Cheap 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 November 19, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$133
(Kiwi.com)

One-way from

$55
(Priceline)

Popular in

November

Cheapest in

August

Average price

$327

Good round-trip deal

$297 or less

Good one-way deal

$161 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. 0% potential increase in price ($0 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 19, 2025.
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 - MDW

INDMDW

Indianapolis

Tue 1/27

12:21 pm-12:05 pm

2 stops24h 44m

Chicago Midway

Mon 2/2

1:00 pm-6:13 pm

1 stop28h 13m

$167

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Thu 1/8

10:38 am-8:05 pm

1 stop10h 27m

Chicago O'Hare Intl

Mon 1/12

4:38 pm-12:18 am

1 stop6h 40m

$175

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Wed 12/24

4:15 pm-4:41 pm

Nonstop1h 26m

Chicago O'Hare Intl

Wed 12/31

10:50 am-1:09 pm

Nonstop1h 19m

$197

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Wed 12/17

10:03 am-10:27 am

Nonstop1h 24m

Chicago O'Hare Intl

Wed 12/24

8:20 am-10:43 am

Nonstop1h 23m

$197

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Mon 1/26

12:38 pm-10:46 pm

1 stop11h 08m

Chicago O'Hare Intl

Tue 2/17

5:32 pm-10:38 pm

1 stop28h 06m

$198

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Tue 12/2

9:03 am-6:46 pm

2 stops10h 43m

Chicago O'Hare Intl

Fri 12/5

8:36 am-7:43 am

1 stop22h 07m

$214

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Tue 12/23

5:15 am-10:18 am

1 stop30h 03m

Chicago O'Hare Intl

Sat 1/24

12:00 pm-10:48 pm

1 stop9h 48m

$218

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Fri 1/23

2:12 pm-8:05 pm

1 stop6h 53m

Chicago O'Hare Intl

Sun 1/25

5:20 pm-10:48 pm

3 stops28h 28m

$221

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Wed 12/3

5:00 am-12:56 pm

1 stop8h 56m

Chicago O'Hare Intl

Sun 12/7

4:49 pm-8:26 pm

1 stop26h 37m

$223

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Mon 1/26

4:25 pm-4:25 pm

Nonstop1h 00m

Chicago Midway

Tue 2/17

1:25 pm-6:00 pm

1 stop3h 35m

$224

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 39 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Indianapolis-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, March is the cheapest month in which you can book a flight from Indianapolis to Chicago (average of $131). 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 November 19, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 33% 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 November 2, 2025.

Travelers seeking maximum savings on their Indianapolis to Chicago flight should consider departing on Sunday at noon 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 November 19, 2025.

The most flights from IND to CHI are scheduled on a Monday (62 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 on average).

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

The best insider tips for Indianapolis to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Indianapolis to Chicago trip
Airports
IND

IND offers fast security lines with an average wait time of less than 3 minutes, making it ideal for business travelers.

Read more about INDby Barbara Noe Kennedy
ORD

For a quick city transfer, take the 'L' train from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

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

Barbara Noe Kennedy

Barbara Noe Kennedy

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 November 19, 2025.
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
4,249 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,025 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,046 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 44 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Indianapolis to Chicago?

    Spirit Airlines, United Airlines, and American Airlines can get you from Indianapolis to Chicago in just under 1h 24m. Your travel time can differ by up to 9h 03m. 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 $141 on this airline. An additional option worth looking into is United Airlines, starting at $188. American Airlines is priced at 48% 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 Frontier. According to our data, you can fly for as low as $81. Users have also found prices from $96 and $99 on Spirit Airlines and United Airlines, 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: Air Chathams (100%), Copa Airlines (90%), Air New Zealand (81%).

  • What are the cheapest flights from Indianapolis to Chicago?

    Looking at all options, your cheapest flight can be booked for $136. While the most popular route (Indianapolis - Chicago O'Hare Intl) can be booked for $158 on average, our data indicates $1,191 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, March is the cheapest month in which you can book a flight from Indianapolis to Chicago (average of $131). 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
Hammond
Porter
Benton Harbor
Merrillville

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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 2 airlines flying from Indianapolis to Chicago

Discover the top 2 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 November 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$141Average$235FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$188Average$289FlexibilityNo cancel feeOn-time69%

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