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

Direct flights offer convenience and save time, but they are not always the most economical choice. Flights with one or more layovers can often be cheaper, especially if you are not in a rush. Consider your priorities for cost versus travel time when deciding.

Can flexible travel dates help on Evansville to Chicago flights?

Yes, being flexible with your travel dates can significantly impact the price of your flight. Mid-week flights or those during off-peak seasons usually offer better value than weekend or holiday travel. Adjusting your departure or return by a day or two may reveal cheaper fares.

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. Factor these into your total travel budget to avoid surprises.

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 today

456 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 31, 2026.)

Today’s best flight deals from Evansville to Chicago

Explore current cheapest deals departing from Evansville to Chicago

2026-09-10 – 2026-10-07
EVV - Chicago
43% AI deal score
$331
$308
Round trip
2027-01-10 – 2027-01-22
EVV - Chicago
41% AI deal score
$322
$319
Round trip
2026-12-06 – 2026-12-11
EVV - Chicago
45% AI deal score
$368
$324
Round trip
2026-10-22 – 2026-11-11
EVV - Chicago
37% AI deal score
$297
$324
Round trip
2026-12-09 – 2026-12-11
EVV - Chicago
45% AI deal score
$372
$325
Round trip
2027-01-10 – 2027-01-29
EVV - Chicago
38% AI deal score
$310
$328
Round trip
2027-01-10 – 2027-01-25
EVV - Chicago
39% AI deal score
$316
$328
Round trip
2026-10-29 – 2026-11-11
EVV - Chicago
38% AI deal score
$315
$328
Round trip
2026-09-20 – 2026-10-07
EVV - Chicago
37% AI deal score
$302
$332
Round trip
2026-09-24 – 2026-10-07
EVV - Chicago
38% AI deal score
$314
$333
Round trip

Evansville to Chicago: Overview

Insights for flights from Evansville to Chicago

Right now, if you're looking for cheap flights from Evansville to Chicago, fares are below the typical level. Recent fares for this route typically range from $619 to $917, with a median of $850. New deals for this route show up several times a week, indicating a regular cadence for price changes.

When is the cheapest time to fly from Evansville to Chicago? Based on recent data, the cheapest month to fly is April, with a median fare of $468. May also offers more affordable options, with a median fare of $509. Fares tend to be higher in June, where the median price rises to $784.

A typical journey from Evansville to Chicago takes approximately 26h 25m, including connections. Most itineraries for this route connect at least once, with the median number of stopovers for connecting flights being 2. There are no direct flights from Evansville to Chicago, so all travel involves at least one stop.

The distance between Evansville and Chicago is 417 kilometers, classifying this as a short-haul route. This means you can expect a relatively short travel distance, though the journey time is extended due to the necessity of connecting flights.

How much is a round trip from Evansville to Chicago

Regular price: $260 - $347

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

Regular prices for this route typically range from $260 to $347. The current lowest deal is $274 with Allegiant Air, for travel between Sep 10 and Oct 7.

now $274

Low $260

High $347

The cheapest time to fly from Evansville to Chicago

The cheapest month to fly from Evansville to Chicago is April, with a median price of $468. The most expensive month is October, with a median price of $930. Prices are generally lower from April to July.

April

Cheapest

Flights from $468

October

Most Expensive

Flights from $930

Apr

May

Jun

Jul

Aug

Oct

Direct flights from Evansville to Chicago

American Airlines

Last-minute flights going from Evansville to Chicago

Thu, Sep 10

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (RFD)

Allegiant Air

$331

$308

One-way

Thu, Sep 10

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (RFD)

Allegiant Air

$396

$431

One-way

Thu, Sep 10

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

American Airlines

$214

$504

One-way

Fri, Sep 11

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

American Airlines

$237

$453

One-way

Sat, Sep 12

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

Breeze Airways

$415

$392

One-way

Sun, Sep 13

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (RFD)

Allegiant Air

$423

$462

One-way

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

3 nights

Dec 6 - Dec 9

$378 → $288

24%

5 nights

Dec 6 - Dec 11

$375 → $326

13%

4 nights

Sep 6 - Sep 10

$423 → $388

27 nights

Sep 10 - Oct 7

$302 → $280

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 $619.

📅 Best time to fly

April offers the lowest median price

Historically, April is the cheapest month to fly, with a median price of $468.

⏱️ Flight duration

Connecting flights average 26h 25m

Flights from Evansville to Chicago typically involve 2 stopovers, lasting 26h 25m.

✈️ Airlines & availability

Connecting flights are dominant on this route

This route is connecting-dominant, with no direct flights available in the last 90 days.

🏆 Airline highlight

American Airlines offers deals on connecting flights

American Airlines has offered connecting flight deals on the Evansville to Chicago route.

🎯 Booking tip

Deals appear regularly for this route

Deals for flights from Evansville to Chicago appear regularly, often within 30 days.

Evansville main airports to depart from

Evansville Regional (EVV)

Cheapest

Fly from Evansville Regional for convenient access to Chicago.

📍 ~10 km from Evansville (reachable by car)

💸 Flights from ~$320

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Fly into Chicago Midway International for a convenient arrival in Chicago from Evansville.

📍 ~15 km from city center (reachable by public transport, car)

💸 Flights from ~$289

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and is easily accessible from Chicago.

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

💸 Flights from ~$292

Business & First Class Flight Deals to Chicago

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

Chicago, United States

28% AI deal score

$2,789

Frequently Asked Questions About Flights to Chicago

To find more affordable flights, consider being flexible with your travel dates and times. Comparing prices across different airlines and booking sites can often reveal better deals. Looking into flights with layovers may also present lower-cost options.

Booking flights in advance, often several weeks or months before your intended departure, can sometimes result in lower fares. Prices may fluctuate, so monitoring them over time can help you identify a good booking window. Weekday travel might also offer better rates than weekend travel.

Comparing nearby airports can sometimes provide additional flight options and potentially lower prices. While it may add to your ground travel time, the savings on airfare could be significant. Always factor in the total cost and convenience when considering alternative airports.

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Evansville to Chicago: Overview

Insights for flights from Evansville to Chicago

How much is a round trip from Evansville to Chicago

Regular price: $260 - $347

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

Regular prices for this route typically range from $260 to $347. The current lowest deal is $274 with Allegiant Air, for travel between Sep 10 and Oct 7.

now $274

Low $260

High $347

The cheapest time to fly from Evansville to Chicago

April

Cheapest

Flights from $468

October

Most Expensive

Flights from $930

Apr

May

Jun

Jul

Aug

Oct

Direct flights from Evansville to Chicago

American Airlines

Last-minute flights going from Evansville to Chicago

Thu, Sep 10

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (RFD)

Allegiant Air

$331

$308

One-way

Thu, Sep 10

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (RFD)

Allegiant Air

$396

$431

One-way

Thu, Sep 10

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

American Airlines

$214

$504

One-way

Fri, Sep 11

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

American Airlines

$237

$453

One-way

Sat, Sep 12

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (ORD)

Breeze Airways

$415

$392

One-way

Sun, Sep 13

⌛ Last-Minute

EVV - Chicago

Evansville (EVV) - Chicago (RFD)

Allegiant Air

$423

$462

One-way

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

3 nights

Dec 6 - Dec 9

$378 → $288

24%

5 nights

Dec 6 - Dec 11

$375 → $326

13%

4 nights

Sep 6 - Sep 10

$423 → $388

27 nights

Sep 10 - Oct 7

$302 → $280

Popular Airports to fly from Evansville to Chicago