Can I fly direct from Indianapolis to Chicago?

Yes, direct flights from Indianapolis to Chicago are available. Historically, approximately 46.3% of flights on this route have been direct. For journeys that involve connecting flights, travelers typically experience a median of 2 stopovers.

How long is the flight from Indianapolis to Chicago?

The direct flight from Indianapolis to Chicago typically takes about 1 hour and 22 minutes, covering a distance of 261 kilometers. For flights with one stop, the median duration is considerably longer, averaging 10 hours and 57 minutes. This difference highlights the efficiency of direct travel on this route.

How often do cheap flights from Indianapolis to Chicago come up?

Historically, cheap flights from Indianapolis to Chicago are classified as frequent. This indicates that travelers typically have regular opportunities to find good deals on this route. The consistent availability of competitive fares makes it a favorable route for budget-conscious planning.

Flights From Indianapolis

To Chicago

Cheap Flights from Indianapolis to Chicago

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Deals from

Indianapolis

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 5 days ago

402 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 12, 2026.)

Today’s best flight deals from Indianapolis to Chicago

Explore current cheapest deals departing from Indianapolis to Chicago

Round trip

Sort by: Cheapest

September 19 - September 26

Cheapest

Best

IND - Chicago

$130

$131

Round trip

September 5 - September 12

Cheapest

IND - Chicago

$126

$131

Round trip

September 22 - September 29

Cheapest

IND - Chicago

$134

$131

Round trip

November 19 - November 26

IND - Chicago

$148

$144

Round trip

August 4 - August 5

Earliest

IND - Chicago

$147

$157

Round trip

August 6 - August 10

IND - Chicago

$154

$157

Round trip

August 24 - August 27

IND - Chicago

$147

$157

Round trip

August 24 - August 31

IND - Chicago

$130

$157

Round trip

August 15 - August 17

IND - Chicago

$141

$157

Round trip

September 3 - September 14

IND - Chicago

$114

$157

Round trip

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Indianapolis to Chicago: Overview

Insights for flights from Indianapolis to Chicago

A typical journey from Indianapolis to Chicago takes about 2h 46m, including connections. Given that 46.3% of recent fares are non-stop, many travelers will experience at least one layover. For itineraries that do include connections, the median number of stopovers is 2.

For travelers seeking cheap flights from Indianapolis to Chicago, prices typically range from $226–$535, with a median of $312. Right now, current fares are above the typical level. Only 1% of recent fares were classified as a good price, indicating that finding lower prices may require flexibility.

The cheapest months to fly from Indianapolis to Chicago are April, with a median fare of $219, followed by October and December, both with median fares of $227. Planning your trip during these months could lead to more favorable pricing.

The distance between Indianapolis and Chicago is 261 km, making this a short-haul route. This short distance contributes to the overall journey time, even with potential connections. New deals for this route appear almost daily, suggesting frequent opportunities to find flights.

How much is a round trip from Indianapolis to Chicago

Regular price: $99 - $224

Prices for flights from Indianapolis to Chicago are currently within the regular range.

The regular price range for flights from Indianapolis to Chicago is between $99 and $224. The current lowest deal is $130 with American Airlines, for travel from Sep 19-Sep 26.

now $130

Low $99

High $224

The cheapest time to fly from Indianapolis to Chicago

The cheapest month to fly from Indianapolis to Chicago is April, with a median price of $219. The most expensive month is February, with a median price of $952. Prices are generally lower from January to December.

April

Cheapest

Flights from $219

February

Most Expensive

Flights from $952

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Indianapolis to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from Indianapolis to Chicago

Sat, Aug 1

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

Southwest Airlines

$265

$269

One-way

Mon, Aug 3

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

Frontier Airlines

$263

$244

One-way

Tue, Aug 4

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

American Airlines

$145

$157

One-way

Wed, Aug 5

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

Frontier Airlines

$261

$175

One-way

Thu, Aug 6

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

Southwest Airlines

$152

$157

One-way

Thu, Aug 6

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

$143

$197

One-way

Biggest price drops on these dates for flights from Indianapolis to Chicago

2 nights

Dec 8 - Dec 10

$304 → $212

30%

7 nights

Aug 12 - Aug 19

$233 → $177

24%

2 nights

Sep 3 - Sep 5

$243 → $192

21%

5 nights

Aug 17 - Aug 22

$241 → $212

12%

Popular Airports to fly from Indianapolis to Chicago

Indianapolis - Chicago route insights

💸 Price insights

Recent fares are below the typical level at $130.

Recent fares are below the typical level. Historically, 25% of fares were cheaper than $130.

📅 Best time to fly

April is historically the cheapest month to fly at $219.

April is historically the cheapest month to fly. February is typically the most expensive month.

⏱️ Flight duration

The median flight time is 2h 46m.

The median flight time for this route is 2 hours and 46 minutes.

✈️ Airlines & availability

46% of recent flights are direct.

46% of recent flights are direct. American Airlines and Southwest Airlines offer direct flights.

🏆 Airline highlight

American Airlines has a deal for $130.

American Airlines has a deal for $130. This deal is for September 19 - September 26.

🎯 Booking tip

Deals appear frequently for this route.

Deals for flights on this route appear frequently, offering good opportunities to save.

Indianapolis main airports to depart from

Indianapolis International (IND)

Cheapest

Indianapolis International offers flights to Chicago, making it a convenient option for your journey.

📍 ~15 km from Indianapolis city center (reachable by car)

💸 Flights from ~$157

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International Airport is a convenient arrival option for flights to Chicago from Indianapolis.

📍 ~15 km from Chicago city center (reachable by car)

💸 Flights from ~$157

Chicago Rockford International (RFD)

Chicago Rockford International Airport offers an alternative arrival point for flights to Chicago from Indianapolis.

📍 ~120 km from Chicago city center (reachable by car)

💸 Flights from ~$243

O Hare International (ORD)

O'Hare International Airport is a major arrival hub for flights to Chicago from Indianapolis.

📍 ~30 km from Chicago city center (reachable by car)

💸 Flights from ~$157

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$203

Gerald R. Ford International (GRR)

Cheapest

Gerald R. Ford International provides a robust domestic network with legacy and low-cost airlines.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$198

Dane County Regional (MSN)

Dane County Regional is a reliable regional hub with efficient operations and good amenities for travelers.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$267

South Bend International (SBN)

South Bend International is the closest alternative airport to the Chicago metro area.

📍 ~120 km from Chicago (reachable by train)

💸 Flights from ~$225

Fort Wayne International (FWA)

Fort Wayne International offers multiple cabin classes and solid connectivity for eastern domestic destinations.

📍 ~220 km from Chicago (reachable by car)

💸 Flights from ~$261

Business & First Class Flight Deals to Chicago

36% AI deal score

$2,407

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Indianapolis to Chicago is typically 14-27 days prior to departure. Flights booked within this period have an average price of $209. Booking 7-13 days out sees an average price of $328, while waiting until 0-6 days before departure can result in an average price of $405. Conversely, booking more than 60 days in advance typically leads to higher average prices, around $447.

Across the trailing quarter, a good price for a flight from Indianapolis to Chicago is considered to be $226 or less. The median price for this route during the same period was $312. Prices can vary, with 75% of observed fares being $535 or less.

Historically, April, October, and December have offered some of the most competitive prices for flights from Indianapolis to Chicago. In April, the median price was $219. Both October and December also showed favorable median prices of $227. This is notably lower than the annual median price for the route, which stands at $312.

Related routes

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