Are direct flights from Evansville to Chicago always the best option?

Direct flights offer convenience by reducing travel time and avoiding layovers. However, they are not always the most economical choice. Flights with connections may sometimes be cheaper, depending on the route and airline. Consider your priorities for cost versus travel time.

Can flexible travel dates help on Evansville to Chicago flights?

Yes, being flexible with your travel dates can often lead to finding more affordable flights. Prices can vary significantly between different days of the week or even specific times. Adjusting your departure or return by a day or two may reveal better deals.

What extra costs should I check before booking Evansville to Chicago flights?

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight services. Some airlines may also charge for printing boarding passes at the airport. Being aware of these additional fees can help you budget accurately for your trip.

Flights From Evansville

To Chicago

Cheap Flights from Evansville to Chicago

Browse current best options from Evansville. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Evansville

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

Prices updated 4 days ago

476 airlines compared

80%+ AI score for best value

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

Today’s best flight deals from Evansville to Chicago

Explore current cheapest deals departing from Evansville to Chicago

2026-12-16 – 2027-01-12
EVV - Chicago
47% AI deal score
$286
$245
Round trip
2026-12-16 – 2027-01-13
EVV - Chicago
47% AI deal score
$286
$247
Round trip
2026-12-16 – 2027-01-12
EVV - Chicago
68% AI deal score
$300
$247
Round trip
2026-12-16 – 2027-01-05
EVV - Chicago
47% AI deal score
$289
$252
Round trip
2026-12-16 – 2027-01-13
EVV - Chicago
48% AI deal score
$300
$252
Round trip
2026-12-16 – 2027-01-05
EVV - Chicago
48% AI deal score
$304
$253
Round trip
2027-01-20 – 2027-01-26
EVV - Chicago
49% AI deal score
$327
$259
Round trip
2027-01-20 – 2027-01-27
EVV - Chicago
48% AI deal score
$327
$263
Round trip
2026-12-12 – 2027-01-05
EVV - Chicago
44% AI deal score
$286
$264
Round trip
2026-12-06 – 2026-12-09
EVV - Chicago
70% AI deal score
$365
$272
Round trip

Evansville to Chicago: Overview

Insights for flights from Evansville to Chicago

Right now, cheap flights from Evansville to Chicago typically range from $650 to $676, with a median fare of $662. Current fares are below the typical level for this route. New deals for this route are infrequent — a price alert helps to stay informed.

When considering the cheapest time to fly from Evansville to Chicago, December stands out with a median fare of $662. August also offers competitive pricing, with a median fare of $943.

The typical journey time from Evansville to Chicago is approximately 26h 25m, including connections. Most itineraries for this route connect at least once, with a median of 2 stopovers when connecting.

The distance between Evansville and Chicago is 417 kilometers, classifying this as a short-haul route.

How much is a round trip from Evansville to Chicago

Regular price: $246 - $433

Prices are currently below the regular range for flights from Evansville to Chicago.

The regular price range for flights from Evansville to Chicago is typically between $246 and $433. The current lowest deal is $245 with Breeze Airways, for travel from Dec 16-Jan 12.

now $245

Low $246

High $433

The cheapest time to fly from Evansville to Chicago

The cheapest month to fly from Evansville to Chicago is December, with a median price of $329. The most expensive month is October, with a median price of $471. Prices are generally lower from January to December.

December

Cheapest

Flights from $329

October

Most Expensive

Flights from $471

Jan

Feb

Oct

Nov

Dec

Direct flights from Evansville to Chicago

Breeze Airways

Frontier Airlines

Allegiant Air

American Airlines

Last-minute flights going from Evansville to Chicago

Fri, Oct 9

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

American Airlines

$341

$591

One-way

Wed, Oct 21

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

American Airlines

$217

$591

One-way

Thu, Oct 29

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (RFD)

Allegiant Air

$312

$263

One-way

Wed, Nov 4

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

Breeze Airways, Frontier Airlines

$354

$251

One-way

Wed, Nov 4

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

Breeze Airways, Frontier Airlines

$375

$256

One-way

Wed, Nov 4

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

Breeze Airways, Frontier Airlines

$299

$296

One-way

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

2 nights

Dec 6 - Dec 8

$368 → $290

21%

13 nights

Oct 29 - Nov 11

$314 → $253

20%

4 nights

Jan 22 - Jan 26

$330 → $271

18%

5 nights

Dec 6 - Dec 11

$359 → $300

16%

Popular Airports to fly from Evansville to Chicago

Evansville - Chicago route insights

💸 Price insights

Recent fares are below the typical level

Recent fares from Evansville to Chicago are below the typical level at $245.

📅 Best time to fly

Fly in December for the best prices

Historically, December offers the lowest median prices at $662 for Evansville to Chicago.

⏱️ Flight duration

Connecting flights take 26h 25m

Flights from Evansville to Chicago typically involve 2 stopovers, with a median duration of 26h 25m.

✈️ Airlines & availability

Connecting flights are dominant

Direct flights are not available; connecting flights are the only option for this route.

🏆 Airline highlight

Breeze Airways offers many deals

Breeze Airways has 92 direct deals, making it a frequent option for this route.

🎯 Booking tip

Deals are rare for this route

Deals for flights from Evansville to Chicago are historically rare, so book when you see a good price.

Evansville main airports to depart from

Evansville Regional (EVV)

Cheapest

Fly from Evansville Regional for direct access to Chicago, offering convenience for local travelers.

📍 ~8 km from Evansville (reachable by car)

💸 Flights from ~$247

Chicago main airports to arrive at

Chicago Rockford International (RFD)

Cheapest

Chicago Rockford International offers a budget-friendly option for travelers flying from Evansville to Chicago.

📍 ~126 km from Chicago (reachable by car)

💸 Flights from ~$246

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International is a major international airport with significant carrier presence and direct flight options.

📍 ~115 km from Chicago (reachable by train or car)

💸 Flights from ~$357

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Evansville to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From EVV

Elite

Oct 08

Chicago, United States

30% AI deal score

$1,891

From EVV

Elite

Nov 20

Chicago, United States

28% AI deal score

$2,504

From EVV

Elite

Oct 09

Chicago, United States

28% AI deal score

$2,537

From EVV

Elite

Oct 13

Chicago, United States

28% AI deal score

$2,537

Frequently Asked Questions About Flights to Chicago

To find more affordable flights, consider being flexible with your travel dates and times. Using flight comparison sites can help you compare options from various providers. Sometimes, booking in advance or looking at different airlines may reveal better deals.

Booking flights usually involves a balance between planning ahead and waiting for potential last-minute deals. Prices can fluctuate, so monitoring fares over time may help you identify a good booking window. Generally, booking several weeks or months in advance can often provide more options.

Comparing nearby airports can sometimes offer more flight options or different price points. While it may add to your ground travel, the potential savings on airfare could be significant. It's often worth checking if alternative airports in the region serve your desired destination.

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Evansville to Chicago: Overview

Insights for flights from Evansville to Chicago

The distance between Evansville and Chicago is 417 kilometers, classifying this as a short-haul route.

How much is a round trip from Evansville to Chicago

Regular price: $246 - $433

Prices are currently below the regular range for flights from Evansville to Chicago.

The regular price range for flights from Evansville to Chicago is typically between $246 and $433. The current lowest deal is $245 with Breeze Airways, for travel from Dec 16-Jan 12.

now $245

Low $246

High $433

The cheapest time to fly from Evansville to Chicago

December

Cheapest

Flights from $329

October

Most Expensive

Flights from $471

Jan

Feb

Oct

Nov

Dec

Direct flights from Evansville to Chicago

Breeze Airways

Frontier Airlines

Allegiant Air

American Airlines

Last-minute flights going from Evansville to Chicago

Fri, Oct 9

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

American Airlines

$341

$591

One-way

Wed, Oct 21

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

American Airlines

$217

$591

One-way

Thu, Oct 29

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (RFD)

Allegiant Air

$312

$263

One-way

Wed, Nov 4

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

Breeze Airways, Frontier Airlines

$354

$251

One-way

Wed, Nov 4

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

Breeze Airways, Frontier Airlines

$375

$256

One-way

Wed, Nov 4

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

Breeze Airways, Frontier Airlines

$299

$296

One-way

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

2 nights

Dec 6 - Dec 8

$368 → $290

21%

13 nights

Oct 29 - Nov 11

$314 → $253

20%

4 nights

Jan 22 - Jan 26

$330 → $271

18%

5 nights

Dec 6 - Dec 11

$359 → $300

16%

Popular Airports to fly from Evansville to Chicago