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$49+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
IND — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:20 pmSDF - ORD
Nonstop1h 38mUnited Airlines
Tue 12/97:55 pmORD - SDF
Nonstop1h 34mUnited Airlines
Deal found 10/30$97
This Southwest deal was found by Cheapflights users on 10/29. 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.
Thu 12/46:45 amSDF - MDW
Nonstop1h 15mSouthwest
Mon 12/810:05 amMDW - SDF
Nonstop1h 25mSouthwest
Deal found 10/29$97
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/87:45 pmIND - MDW
1 stop14h 01mFrontier
Thu 12/117:23 pmMDW - IND
1 stop18h 47mFrontier
Deal found 10/28$133
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/69:00 amSDF - ORD
Nonstop1h 40mUnited Airlines
Mon 12/87:55 pmORD - SDF
Nonstop1h 34mUnited Airlines
Deal found 10/28$134
This Southwest deal was found by Cheapflights users on 10/28. 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 12/67:10 amSDF - MDW
Nonstop1h 20mSouthwest
Mon 12/88:50 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 10/28$134
This Kiwi.com deal was found by Cheapflights users on 10/27. 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
1 stop24h 54mFrontier
Tue 12/306:00 amORD - IND
1 stop10h 44mFrontier
Deal found 10/27$138
This Frontier deal was found by Cheapflights users on 10/27. 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 11/147:09 pmIND - ORD
1 stop6h 50mFrontier
Mon 12/1511:01 amORD - IND
1 stop8h 25mFrontier
Deal found 10/27$143
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/135:05 amIND - ORD
1 stop8h 40mMultiple Airlines
Sat 11/1511:35 amORD - IND
1 stop8h 45mMultiple Airlines
Deal found 10/28$146
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/54:10 pmIND - MDW
1 stop22h 49mFrontier
Mon 12/812:35 pmMDW - IND
1 stop6h 51mFrontier
Deal found 10/29$146
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/89:11 pmIND - ORD
1 stop17h 47mMultiple Airlines
Thu 12/114:47 pmORD - IND
1 stop18h 12mMultiple Airlines
Deal found 10/28$153
This Booking.com deal was found by Cheapflights users on 10/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/139:49 amIND - ORD
1 stop14h 39mFrontier
Fri 11/146:00 amORD - IND
1 stop12h 44mFrontier
Deal found 10/29$155
This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 12/156:16 pmSDF - ORD
1 stop6h 45mDelta
Wed 12/179:49 amORD - SDF
1 stop6h 27mDelta
Deal found 10/28$157

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(United Airlines)

One-way from

$49
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$266

Good round-trip deal

$283 or less

Good one-way deal

$163 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 Indiana to Chicago (CHI)
Search Deals
One-way flight from Indiana to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($18 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 October 2025
Search Deals
Price to beat on a round-trip flight from Indiana to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Indiana to Chicago (CHI).
Search Deals

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 October 30, 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

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 12/3

12:20 pm-12:58 pm

Nonstop1h 38m

Chicago O'Hare Intl

Tue 12/9

7:55 pm-10:29 pm

Nonstop1h 34m

$97

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 12/4

6:21 pm-7:16 pm

Nonstop1h 55m

Chicago O'Hare Intl

Mon 12/8

8:20 pm-10:56 pm

Nonstop1h 36m

$97

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Mon 12/15

7:00 am-7:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Wed 12/17

9:05 am-11:32 am

Nonstop1h 27m

$97

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 12/4

11:45 am-8:45 pm

2 stops10h 00m

Chicago Midway

Mon 12/8

10:05 am-12:30 pm

Nonstop1h 25m

$112

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 12/6

7:10 am-7:30 am

Nonstop1h 20m

Chicago Midway

Mon 12/8

8:50 pm-11:05 pm

Nonstop1h 15m

$134

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sat 12/6

9:00 am-9:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Mon 12/8

7:55 pm-10:29 pm

Nonstop1h 34m

$134

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 12/23

5:35 pm-11:05 pm

1 stop6h 30m

Chicago Midway

Tue 12/30

9:30 am-11:45 am

Nonstop1h 15m

$144

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Mon 12/15

6:16 pm-12:01 am

1 stop6h 45m

Chicago O'Hare Intl

Wed 12/17

9:49 am-5:16 pm

1 stop6h 27m

$157

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 12/4

6:16 pm-12:01 am

1 stop6h 45m

Chicago O'Hare Intl

Mon 12/8

2:30 pm-9:13 pm

1 stop5h 43m

$157

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Mon 12/15

2:29 pm-6:27 pm

1 stop4h 58m

Chicago O'Hare Intl

Tue 12/16

11:15 am-7:12 pm

1 stop6h 57m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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 $135). Flying from Indiana to Chicago in April is currently the most expensive (average of $191). 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 October 30, 2025.

It’s typically best to fly out from Indiana to Chicago in the morning. Doing so could potentially save you 29% on the flight price compared to flying at noon, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Indiana to Chicago. Price data was last updated on October 26, 2025.

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

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.

  • How long is the flight from Indiana to Chicago?

    For as low as $97, United Airlines can have you in Chicago from Indiana in 1h 38m. There are 287 mi between Indiana and Chicago. This flight may include one or multiple stops.

  • 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 $49. However, be on the lookout for offers from Southwest and Frontier, 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 Louisville Intl - Chicago O'Hare Intl or Indianapolis - 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 Air Chathams (100%), Copa Airlines (95%) and Finnair (91%).

  • What are the cheapest flights from Indiana to Chicago?

    Looking at all options, your cheapest flight can be booked for $136. While the most popular route (Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl) can be booked for $177 on average, our data indicates $850 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 $135). Flying from Indiana to Chicago in April is currently the most expensive (average of $191). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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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.
John F Kennedy Intl to O'Hare Intl flights
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Dallas/Fort Worth to Midway flights
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Atlanta to Midway flights
LaGuardia to Midway flights
Newark to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Newark to St. Louis flights
Denver to Midway flights
Philadelphia to Midway flights
Charlotte to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
San Francisco to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to Midway flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Minneapolis to Midway flights
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Santa Ana to O'Hare Intl flights
John F Kennedy Intl to St. Louis flights
Reagan-National to Midway flights
Austin to O'Hare Intl flights
Cleveland to O'Hare Intl flights
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Hartford to O'Hare Intl flights
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LaGuardia to St. Louis flights
Boston to Midway flights

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$140Average$309FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$160Average$250FlexibilityNo cancel feeOn-time69%
Southern / MokuleleCheapest$189Average$302FlexibilityNo cancel feeOn-timeN/A

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