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Cheap Flights from Indianapolis to Chicago

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Indianapolis

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

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Indianapolis to Chicago

Explore current cheapest deals departing from Indianapolis to Chicago

Round trip

Sort by: Cheapest

July 7 - July 15

Cheapest

Earliest

IND - Chicago

$132

$157

Round trip

July 15 - July 22

Cheapest

IND - Chicago

$133

$157

Round trip

October 7 - October 14

Cheapest

Best

IND - Chicago

$154

$157

Round trip

July 7 - July 14

Cheapest

Earliest

IND - Chicago

$135

$157

Round trip

July 14 - July 15

Cheapest

IND - Chicago

$138

$157

Round trip

July 14 - July 21

Cheapest

IND - Chicago

$133

$157

Round trip

July 21 - July 22

Cheapest

IND - Chicago

$147

$157

Round trip

August 5 - August 12

Cheapest

IND - Chicago

$138

$157

Round trip

August 12 - August 26

Cheapest

IND - Chicago

$125

$157

Round trip

October 6 - October 7

Cheapest

IND - Chicago

$164

$157

Round trip

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Route Intelligence — 486,190 Searches this Week

Insights for flights from Indianapolis to Chicago

A typical journey from Indianapolis to Chicago takes about 2h 46m, including connecting itineraries. Given that a meaningful share of flights on this route involve connections, this duration accounts for the total travel time from departure to arrival. This is a relatively short travel time, making Chicago an accessible destination from Indianapolis.

For travelers seeking cheap flights from Indianapolis to Chicago, fares typically range from $218–$406, with a median of $271. Right now, current fares are below the typical level for this route. However, 0% of recent fares were classified as a good price, indicating that finding exceptional deals might require careful timing and flexibility. New deals appear almost daily, so setting up a price alert can be beneficial.

When is the cheapest time to fly from Indianapolis to Chicago? The data indicates that April is typically the most affordable month, with a median fare of $219. Other cost-effective options include October and December, both showing a median fare of $227. Planning your trip during these months could lead to more favorable prices.

Regarding direct flights from Indianapolis to Chicago, 52.1% of recent fares were for non-stop itineraries. This means a meaningful share are non-stop, while the remaining itineraries typically involve 2 connections. Travelers prioritizing convenience may want to focus on securing one of the available direct flights, though connecting options are also widely available.

The distance between Indianapolis and Chicago is 261 km, classifying this as a short-haul route. This short distance contributes to the relatively brief overall journey time, even with connections. Short-haul flights generally offer more frequent departures and a wider range of scheduling options for travelers.

How much is a round trip from Indianapolis to Chicago

Regular price: $107 - $255

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 $107 and $255. The current lowest deal is $157 with American Airlines. This deal is for travel from Jul 7-Jul 15.

now $157

Low $107

High $255

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

Tue, Jul 7

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

American Airlines

$132

$157

One-way

Tue, Jul 7

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

$135

$157

One-way

Wed, Jul 8

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

United Airlines

$135

$227

One-way

Mon, Jul 13

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

$152

$237

One-way

Tue, Jul 14

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

$138

$157

One-way

Tue, Jul 14

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

$133

$157

One-way

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

6 nights

Sep 30 - Oct 6

$270 → $195

28%

1 night

Sep 14 - Sep 15

$259 → $203

22%

13 nights

Sep 30 - Oct 13

$247 → $195

21%

8 nights

Sep 14 - Sep 22

$241 → $202

16%

Popular Airports to fly from Indianapolis to Chicago

Indianapolis - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Indianapolis to Chicago are below the typical level at $157.

📅 Best time to fly

April is historically the cheapest month

Historically, April is the cheapest month to fly from Indianapolis to Chicago, with a median price of $219.

⏱️ Flight duration

Typical flight time is 2h 46m

The typical flight duration from Indianapolis to Chicago is 2 hours and 46 minutes.

✈️ Airlines & availability

Frequent deals are available

Deals for flights from Indianapolis to Chicago are frequent, with over 1 deal per day.

🏆 Airline highlight

American Airlines offers direct flights

American Airlines is one of the airlines offering direct flights from Indianapolis to Chicago.

🎯 Booking tip

Consider booking in April

For the best prices, consider booking your flight to Chicago in April, when the median price is $219.

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 high-frequency flights and direct rail access, making it a strong alternative.

📍 ~135 km from Chicago (reachable by rail and car)

💸 Flights from ~$252

South Bend International (SBN)

Cheapest

South Bend International is the closest alternative to Chicago with direct commuter rail access.

📍 ~125 km from Chicago (reachable by rail)

💸 Flights from ~$233

Gerald R. Ford International (GRR)

Gerald R. Ford International is a major regional hub, good for travelers on Chicago's eastern side.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$234

Dane County Regional (MSN)

Dane County Regional is a reliable, less congested option with consistent service levels.

📍 ~200 km from Chicago (reachable by car)

💸 Flights from ~$279

Fort Wayne International (FWA)

Fort Wayne International provides stable regional service for travelers in southeastern Chicago suburbs.

📍 ~235 km from Chicago (reachable by car)

💸 Flights from ~$268

Business & First Class Flight Deals to Chicago

36% AI deal score

$2,407

Frequently Asked Questions About Flights to Chicago

Historically, the best prices for flights from Indianapolis to Chicago are found by booking 14-27 days in advance. During this period, the average price is typically around $209. Booking within 0-6 days of departure usually results in higher prices, averaging $405. Similarly, booking more than 60 days out also tends to be more expensive, with an average price of $447.

Across the trailing quarter, a good price for a flight from Indianapolis to Chicago is considered to be $218 or less. The median price for this route has been $271. Prices can range significantly, with 75% of observed prices being $406 or less.

Historically, April, October, and December have offered some of the cheapest flights from Indianapolis to Chicago. The median price in April was $219, while October and December both had a median price of $227. These prices are generally lower than the annual median price of $271 for this route.

Related routes

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