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
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Prices updated 24 days ago
486,190 searches this week
171 airlines compared
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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 Evansville to Chicago
Explore current cheapest deals departing from Evansville to Chicago
Round trip
Sort by: Cheapest
December 6 - December 11
EVV - Chicago
$390
$320
Round trip
December 6 - December 14
EVV - Chicago
$387
$334
Round trip
August 1 - August 21
EVV - Chicago
$297
$335
Round trip
August 27 - August 29
EVV - Chicago
$347
$398
Round trip
August 2 - August 21
EVV - Chicago
$280
$404
Round trip
July 11 - July 18
EVV - Chicago
$236
$406
Round trip
July 15 - July 22
EVV - Chicago
$378
$414
Round trip
August 3 - August 21
EVV - Chicago
$282
$425
Round trip
October 1 - October 3
EVV - Chicago
$407
$432
Round trip
July 23 - July 25
EVV - Chicago
$400
$444
Round trip
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Route Intelligence — 486,190 Searches this Week
How much is a round trip from Evansville to Chicago
Regular price: $329 - $410
Prices are currently below the regular range.
The regular price range for flights from Evansville to Chicago is typically between $329 and $410. The current lowest deal is $320 with Allegiant Air, for travel from Dec 6-Dec 11.
now $320
Low $329
High $410
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
Flights from $468
October
Flights from $930
Direct flights from Evansville to Chicago
American Airlines
Last-minute flights going from Evansville to Chicago
Wed, Jun 17
EVV - Chicago
Evansville (EVV) - Chicago (MDW)
$399
$1,569
One-way
Wed, Jun 17
EVV - Chicago
Evansville (EVV) - Chicago (MDW)
$445
$1,594
One-way
Wed, Jun 17
EVV - Chicago
Evansville (EVV) - Chicago (MDW)
$529
$1,607
One-way
Fri, Jun 19
EVV - Chicago
Evansville (EVV) - Chicago (MDW)
$523
$1,595
One-way
Sat, Jun 20
EVV - Chicago
Evansville (EVV) - Chicago (ORD)
$416
$1,599
One-way
Tue, Jun 23
EVV - Chicago
Evansville (EVV) - Chicago (ORD)
American Airlines
$271
$448
One-way
Biggest price drops on these dates for flights from Evansville to Chicago
Dec 6 - Dec 11
$390 → $320
18%
Dec 6 - Dec 14
$387 → $334
14%
Oct 1 - Oct 3
$407 → $432
6%
Jul 15 - Jul 22
$378 → $414
10%
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, with deals around $320.
📅 Best time to fly
April is historically the cheapest month
Historically, April is the cheapest month to fly from Evansville to Chicago, with a median price of $468.
⏱️ Flight duration
Connecting flights average 26h 25m
Flights from Evansville to Chicago typically involve connections, with a median flight time of 26h 25m.
✈️ Airlines & availability
Connecting flights are dominant
This route is dominated by connecting flights, with 0% direct flights historically available.
🏆 Airline highlight
American Airlines offers direct deals
American Airlines has historically offered direct deals on flights from Evansville to Chicago.
🎯 Booking tip
Deals appear regularly
Deals for flights from Evansville to Chicago appear regularly, about 0.17 deals per day.
Evansville main airports to depart from
Evansville Regional (EVV)
Evansville Regional Airport is a convenient option for flights from Evansville to Chicago.
📍 ~10 km from Evansville (reachable by car)
💸 Flights from ~$320
Chicago main airports to arrive at
Chicago Midway International (MDW)
Chicago Midway International is a convenient arrival airport for flights to Chicago from Evansville.
📍 ~15 km from city center (reachable by car)
💸 Flights from ~$289
Chicago Rockford International (RFD)
Chicago Rockford International offers an alternative arrival option for your trip to Chicago.
📍 ~120 km from city center (reachable by car)
💸 Flights from ~$320
O Hare International (ORD)
O Hare International is a major hub for travelers flying to Chicago from Evansville.
📍 ~25 km from city center (reachable by car)
💸 Flights from ~$289
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by rail; travel time can be affected by heavy traffic on the I-94 corridor)
💸 Flights from ~$356
South Bend International (SBN)
South Bend International is geographically the closest alternative to Chicago, with direct commuter rail connections.
📍 ~120 km from Chicago (reachable by rail; fewer direct flight destinations compared to Milwaukee or Chicago)
💸 Flights from ~$221
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes for travelers.
📍 ~200 km from Chicago (requires a significant drive, over 2 hours, from central Chicago)
💸 Flights from ~$245
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service levels and less congestion.
📍 ~210 km from Chicago (distance exceeds 190km, making it a secondary choice to MKE)
💸 Flights from ~$357
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service and is an alternative for southeastern Chicago suburbs.
📍 ~240 km from Chicago (significant distance from Chicago and limited flight frequency)
💸 Flights from ~$273
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
Jul 10
Chicago, United States
28% AI deal score
$2,511
From EVV
Elite
Jun 19
Chicago, United States
28% AI deal score
$2,565
From EVV
Elite
Jun 23
Chicago, United States
28% AI deal score
$2,579
From EVV
Elite
Jun 26
Chicago, United States
28% AI deal score
$2,579
From EVV
Elite
Jun 28
Chicago, United States
28% AI deal score
$2,603