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 5 days ago
402 airlines compared
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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 Evansville to Chicago
Explore current cheapest deals departing from Evansville to Chicago
Round trip
Sort by: Cheapest
September 24 - October 7
EVV - Chicago
$319
$250
Round trip
November 11 - November 17
EVV - Chicago
$407
$254
Round trip
October 29 - November 17
EVV - Chicago
$341
$260
Round trip
November 11 - December 7
EVV - Chicago
$364
$269
Round trip
December 6 - December 11
EVV - Chicago
$397
$277
Round trip
December 6 - December 14
EVV - Chicago
$383
$279
Round trip
November 11 - December 11
EVV - Chicago
$364
$294
Round trip
November 11 - December 4
EVV - Chicago
$364
$327
Round trip
December 6 - December 9
EVV - Chicago
$401
$329
Round trip
December 10 - December 14
EVV - Chicago
$400
$330
Round trip
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Evansville to Chicago: Overview
How much is a round trip from Evansville to Chicago
Regular price: $272 - $342
Prices for flights from Evansville to Chicago are currently below the regular range.
The regular price range for flights from Evansville to Chicago is typically between $272 and $342. The current lowest deal is $250 with Allegiant Air, for travel from Sep 24-Oct 7.
now $250
Low $272
High $342
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
Mon, Jul 13
EVV - Chicago
Evansville (EVV) - Chicago (ORD)
American Airlines
$294
$542
One-way
Mon, Jul 13
EVV - Chicago
Evansville (EVV) - Chicago (MDW)
$588
$1,603
One-way
Fri, Jul 17
EVV - Chicago
Evansville (EVV) - Chicago (ORD)
$527
$1,608
One-way
Fri, Jul 24
EVV - Chicago
Evansville (EVV) - Chicago (ORD)
American Airlines
$280
$543
One-way
Mon, Jul 27
EVV - Chicago
Evansville (EVV) - Chicago (ORD)
$396
$731
One-way
Mon, Jul 27
EVV - Chicago
Evansville (EVV) - Chicago (ORD)
$404
$1,529
One-way
Biggest price drops on these dates for flights from Evansville to Chicago
Dec 6 - Dec 11
$396 → $296
25%
Dec 6 - Dec 14
$382 → $305
20%
Sep 24 - Oct 7
$324 → $253
22%
Jul 6 - Jul 8
$591 → $522
12%
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 $250.
📅 Best time to fly
April is historically the cheapest month
Historically, April is the cheapest month to fly, with a median price of $468.
⏱️ Flight duration
Flights typically take 26h 25m
Flights from Evansville to Chicago typically take 26h 25m, with 2 stopovers.
✈️ Airlines & availability
Connecting flights are dominant
Connecting flights are dominant on this route, with 0% direct flights available.
🏆 Airline highlight
American Airlines has direct flights
American Airlines offers direct flights from Evansville to Chicago.
🎯 Booking tip
Deals appear regularly
Deals on this route appear regularly, so consider booking when you see a good price.
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 significant carrier presence and direct flight options for Chicago travelers.
📍 ~135 km from Chicago (reachable by car or train), requires travel across state lines.
💸 Flights from ~$311
Gerald R. Ford International (GRR)
Gerald R. Ford International is Michigan's second largest airport with a robust domestic network.
📍 ~200 km from Chicago (reachable by car).
💸 Flights from ~$289
Dane County Regional (MSN)
Dane County Regional is a reliable regional hub with efficient operations and good amenities for Chicago travelers.
📍 ~200 km from Chicago (reachable by car).
💸 Flights from ~$324
South Bend International (SBN)
South Bend International is the closest alternative airport to the Chicago metro area.
📍 ~120 km from Chicago (reachable by car or train).
💸 Flights from ~$229
Fort Wayne International (FWA)
Fort Wayne International offers solid connectivity for travelers heading to eastern domestic destinations.
📍 ~240 km from Chicago (reachable by car).
💸 Flights from ~$316
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