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$39+ Cheap flights from Indiana 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
IND — CHI
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheap flight deals from Indiana to Chicago

Keep the following information in mind while searching for Indiana to Chicago flight deals. Data was last updated April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(Southwest)

One-way from

$39
(United Airlines)

Popular in

March

Cheapest in

December

Average price

$295

Good round-trip deal

$278 or less

Good one-way deal

$89 or less
Provider with most accurate pricing for Indianapolis-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Indianapolis-Chicago (CHI) flights.
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From Indiana to Chicago (CHI)
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One-way flight from Indiana to Chicago (CHI)
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Highest demand for flights based on searches. 10% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Indiana to Chicago (CHI).
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Price to beat on a one-way flight from Indiana to Chicago (CHI).
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Find flight deals from Indiana to Chicago

Cheapest flights from Indiana to Chicago
Explore the most affordable flight options available from Indiana to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Southwest deal was found by Cheapflights users on 4/23. 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 7/97:25 pmIND - MDW
1 stop4h 35mSouthwest
Thu 7/105:35 amMDW - IND
1 stop5h 05mSouthwest
Deal found 4/23$97
This Southwest deal was found by Cheapflights users on 4/22. 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 9/178:15 amIND - ORD
1 stop4h 35mSouthwest
Thu 9/251:50 pmORD - IND
1 stop8h 30mSouthwest
Deal found 4/22$102
This American Airlines deal was found by Cheapflights users on 4/22. 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 5/145:45 amSDF - ORD
Nonstop1h 35mAmerican Airlines
Sat 5/178:25 pmORD - SDF
Nonstop1h 36mAmerican Airlines
Deal found 4/22$121
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Sat 5/175:25 amCVG - ORD
Nonstop1h 28mAmerican Airlines
Mon 5/1910:10 pmORD - CVG
Nonstop1h 19mAmerican Airlines
Deal found 4/23$121
This Southwest deal was found by Cheapflights users on 4/22. 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 5/146:25 amSDF - MDW
Nonstop1h 15mSouthwest
Sat 5/176:40 amMDW - SDF
1 stop6h 20mSouthwest
Deal found 4/22$124
This Southwest deal was found by Cheapflights users on 4/22. 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 6/76:40 pmCVG - MDW
Nonstop1h 10mSouthwest
Tue 6/106:10 pmMDW - CVG
1 stop4h 10mSouthwest
Deal found 4/22$124
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 6/57:00 amSDF - ORD
Nonstop1h 37mUnited Airlines
Fri 6/62:48 pmORD - SDF
Nonstop1h 31mUnited Airlines
Deal found 4/23$125
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 5/152:10 pmCVG - ORD
Nonstop1h 28mUnited Airlines
Fri 5/166:15 pmORD - CVG
Nonstop1h 23mUnited Airlines
Deal found 4/23$125
This Southwest deal was found by Cheapflights users on 4/22. 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.
Mon 5/196:15 amSDF - ORD
1 stop6h 35mSouthwest
Wed 5/211:50 pmORD - SDF
1 stop7h 45mSouthwest
Deal found 4/22$150
This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/157:51 pmCVG - ORD
1 stop10h 19mFrontier
Fri 5/169:00 amORD - CVG
1 stop8h 56mFrontier
Deal found 4/23$155
This Frontier deal was found by Cheapflights users on 4/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/155:45 amCVG - MDW
1 stop7h 39mFrontier
Fri 5/161:19 pmMDW - CVG
1 stop10h 40mFrontier
Deal found 4/23$160
This Frontier deal was found by Cheapflights users on 4/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/164:16 pmIND - ORD
1 stop7h 55mFrontier
Sat 5/248:04 amORD - IND
1 stop4h 50mFrontier
Deal found 4/22$161

Cheapflights Fare Finder

Customize your flight search to find flights from Indiana 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 April 24, 2025.
Use the filters below to find and compare flights from Indiana to Chicago that are best for you.

Fly from

Indiana

Fly to

Chicago

Route

Depart

Return

Price

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 7/9

7:25 pm-11:00 pm

1 stop4h 35m

Chicago Midway

Thu 7/10

5:35 am-11:40 am

1 stop5h 05m

$97

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 5/14

5:45 am-6:20 am

Nonstop1h 35m

Chicago O'Hare Intl

Sat 5/17

8:25 pm-11:01 pm

Nonstop1h 36m

$121

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 5/17

5:25 am-5:53 am

Nonstop1h 28m

Chicago O'Hare Intl

Mon 5/19

10:10 pm-12:29 am

Nonstop1h 19m

$121

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 5/14

6:25 am-6:40 am

Nonstop1h 15m

Chicago Midway

Sat 5/17

6:40 am-2:00 pm

1 stop6h 20m

$124

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 6/7

6:40 pm-6:50 pm

Nonstop1h 10m

Chicago Midway

Tue 6/10

6:10 pm-11:20 pm

1 stop4h 10m

$124

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 6/5

7:00 am-7:37 am

Nonstop1h 37m

Chicago O'Hare Intl

Fri 6/6

2:48 pm-5:19 pm

Nonstop1h 31m

$125

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 5/15

2:10 pm-2:38 pm

Nonstop1h 28m

Chicago O'Hare Intl

Fri 5/16

4:30 pm-7:00 pm

Nonstop1h 30m

$125

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Mon 5/19

6:15 am-11:50 am

1 stop6h 35m

Chicago O'Hare Intl

Wed 5/21

1:50 pm-10:35 pm

1 stop7h 45m

$150

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 5/15

7:51 pm-5:10 am

1 stop10h 19m

Chicago O'Hare Intl

Fri 5/16

9:00 am-6:56 pm

1 stop8h 56m

$155

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 5/15

5:45 am-12:24 pm

1 stop7h 39m

Chicago Midway

Fri 5/16

1:19 pm-12:59 am

1 stop10h 40m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 results
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Best time to book a flight from Indiana to Chicago

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

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

Currently, August is the cheapest month in which you can book a flight from Indiana to Chicago (average of $245). Flying from Indiana to Chicago in March is currently the most expensive (average of $321). 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 IN to CHI?

Find hourly flight availability from Indiana 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 April 24, 2025.

When flying from Indiana to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Indiana to Chicago

Explore weekly flight availability from Indiana 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 April 24, 2025.

The most flights from USIN to CHI are scheduled on a Wednesday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 24, 2025.
To help decide which airline to fly from Indiana to Chicago, see what other customers have to say about Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from Indiana to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $39. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Indiana to Chicago for a low price.

  • What are the most popular routes from Indiana to Chicago?

    While some choose either Cincinnati Cinci./N. Kentucky - Chicago Midway or Louisville Intl - Chicago O'Hare Intl, Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl is the most popular route from Indiana to Chicago.

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

    The top 3 most reliable airlines when flying from Indiana to Chicago are Copa Airlines (95%), SkyWest Airlines (88%) and ANA (88%).

  • What are the cheapest flights from Indiana to Chicago?

    Looking at all options, your cheapest flight can be booked for $147. While the most popular route (Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl) can be booked for $77 on average our data indicates $943 when flying from Indiana to Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Indiana 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 Indiana to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Indiana to Chicago (average of $245). Flying from Indiana to Chicago in March is currently the most expensive (average of $321). 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 Indiana?

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

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Alternative routes for Indiana to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Reagan-National to Midway flights
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Los Angeles to Midway flights
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Newark to St. Louis flights
Philadelphia to Midway flights
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Minneapolis to Midway flights
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Hobby to Midway flights
John F Kennedy Intl to St. Louis flights
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Top 3 airlines flying from Indiana to Chicago

Discover the top 3 airlines that operate flights from Indiana 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$281FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$319FlexibilityNo cancel feeOn-time71%
Southern / MokuleleCheapest$189Average$228FlexibilityNo cancel feeOn-timeN/A

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