Cheap Flights from Philadelphia to Chicago
Browse current best options from Philadelphia. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Philadelphia
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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 Philadelphia to Chicago
Explore current cheapest deals departing from Philadelphia to Chicago
Round trip
Sort by: Cheapest
August 1 - August 8
PHL - Chicago
$122
$143
Round trip
August 8 - August 15
PHL - Chicago
$122
$145
Round trip
August 15 - August 29
PHL - Chicago
$110
$150
Round trip
September 5 - September 6
PHL - Chicago
$127
$150
Round trip
October 11 - November 5
PHL - Chicago
$228
$150
Round trip
October 25 - November 5
PHL - Chicago
$240
$150
Round trip
August 8 - August 14
PHL - Chicago
$122
$154
Round trip
August 10 - August 13
PHL - Chicago
$129
$155
Round trip
August 24 - August 31
PHL - Chicago
$125
$156
Round trip
July 18 - July 25
PHL - Chicago
$131
$157
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Philadelphia to Chicago
How much is a round trip from Philadelphia to Chicago
Regular price: $94 - $224
Prices for flights from Philadelphia to Chicago are currently within the regular range.
The regular price range for flights from Philadelphia to Chicago is between $94 and $224. The current lowest deal is $143 with Frontier Airlines for travel from Aug 1-Aug 8.
now $143
Low $94
High $224
The cheapest time to fly from Philadelphia to Chicago
The cheapest month to fly from Philadelphia to Chicago is September, with a median price of $164. The most expensive month is July, with a median price of $284. Prices are generally lower from January to November.
September
Flights from $164
July
Flights from $284
Direct flights from Philadelphia to Chicago
Frontier Airlines
Last-minute flights going from Philadelphia to Chicago
Tue, Jun 16
PHL - Chicago
Philadelphia (PHL) - Chicago (MDW)
Frontier Airlines
$351
$260
One-way
Tue, Jun 16
PHL - Chicago
Philadelphia (PHL) - Chicago (MDW)
Frontier Airlines
$416
$290
One-way
Wed, Jun 17
PHL - Chicago
Philadelphia (PHL) - Chicago (MDW)
Frontier Airlines
$411
$286
One-way
Wed, Jun 17
TTN - Chicago
Trenton (TTN) - Chicago (ORD)
Frontier Airlines
$470
$291
One-way
Fri, Jun 19
PHL - Chicago
Philadelphia (PHL) - Chicago (ORD)
Frontier Airlines
$351
$251
One-way
Fri, Jun 19
PHL - Chicago
Philadelphia (PHL) - Chicago (ORD)
Frontier Airlines
$390
$252
One-way
Biggest price drops on these dates for flights from Philadelphia to Chicago
Jun 17 - Jun 21
$470 → $291
38%
Jun 19 - Jun 22
$390 → $252
35%
Jun 16 - Jun 18
$416 → $290
30%
Jun 17 - Jun 20
$411 → $286
30%
Popular Airports to fly from Philadelphia to Chicago
Philadelphia - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Philadelphia to Chicago are below the typical level at $143.
📅 Best time to fly
Fly in October or September for the best prices
Historically, October and September offer the lowest median prices at $164.
⏱️ Flight duration
Typical flight duration is 5h 5m
The median flight duration for this route is 5 hours and 5 minutes.
✈️ Airlines & availability
Frontier Airlines offers direct flights
Frontier Airlines has direct flights available for the Philadelphia to Chicago route.
🏆 Airline highlight
Frontier Airlines has the lowest recent fare
Frontier Airlines recently offered a fare of $143 from Philadelphia to Chicago.
🎯 Booking tip
Deals are frequent on this route
Historically, deals for this route appear frequently, more than once per day.
Philadelphia main airports to depart from
Philadelphia International (PHL)
Philadelphia International Airport is a convenient departure point for flights from Philadelphia to Chicago.
📍 ~10 km from city center (reachable by car or train)
💸 Flights from ~$143
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a good option for flights from Philadelphia to Chicago.
📍 ~20 km from Chicago city center (reachable by car)
💸 Flights from ~$143
Chicago Midway International (MDW)
Chicago Midway International Airport is an alternative for your flight to Chicago from Philadelphia.
📍 ~14 km from Chicago city center (reachable by car)
💸 Flights from ~$185
Chicago Rockford International (RFD)
Consider Chicago Rockford International Airport for flights to the wider Chicago area from Philadelphia.
📍 ~110 km from Chicago city center (reachable by car)
💸 Flights from ~$208
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers high-frequency flight options and direct rail access to Chicago.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$245
South Bend International (SBN)
South Bend International is the closest alternative to Chicago with direct commuter rail connections.
📍 ~120 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.
📍 ~225 km from Chicago (reachable by car)
💸 Flights from ~$60
Dane County Regional (MSN)
Dane County Regional is a reliable, less congested alternative with a full range of cabin classes.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$269
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service for travelers in Chicago's southeastern suburbs.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$231
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Philadelphia to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From PHL
Elite
Aug 11
Chicago, United States
78% AI deal score
$1,227
$597
Save $630
From PHL
Elite
Aug 13
Chicago, United States
78% AI deal score
$1,662
$836
Save $826
From PHL
Elite
Jul 22
Chicago, United States
77% AI deal score
$1,104
$535
Save $569
From PHL
Elite
Aug 11
Chicago, United States
77% AI deal score
$1,229
$615
Save $614
From PHL
Elite
Aug 13
Chicago, United States
77% AI deal score
$1,682
$648
Save $1,034
From PHL
Elite
Jun 29
Chicago, United States
76% AI deal score
$1,171
$589
Save $582
From PHL
Elite
Aug 11
Chicago, United States
76% AI deal score
$1,212
$640
Save $572
From PHL
Elite
Aug 12
Chicago, United States
76% AI deal score
$1,220
$640
Save $580
From PHL
Elite
Jun 30
Chicago, United States
76% AI deal score
$1,453
$647
Save $806
From PHL
Elite
Aug 10
Chicago, United States
76% AI deal score
$1,185
$648
Save $537
From PHL
Elite
Aug 15
Chicago, United States
76% AI deal score
$1,219
$651
Save $568
From PHL
Elite
Aug 13
Chicago, United States
76% AI deal score
$1,625
$713
Save $912
From PHL
Elite
Oct 02
Chicago, United States
76% AI deal score
$1,305
$738
Save $567
From PHL
Elite
Jul 04
Chicago, United States
75% AI deal score
$919
$582
Save $337
From PHL
Elite
Aug 09
Chicago, United States
75% AI deal score
$1,185
$664
Save $521
From PHL
Elite
Sep 11
Chicago, United States
74% AI deal score
$5,247
$3,068
Save $2,179
From PHL
Elite
Jul 01
Chicago, United States
74% AI deal score
$693
$547
Save $146
From PHL
Elite
Aug 09
Chicago, United States
74% AI deal score
$1,132
$689
Save $443
From PHL
Elite
Jun 30
Chicago, United States
74% AI deal score
$631
$529
Save $102
From PHL
Elite
Sep 02
Chicago, United States
73% AI deal score
$891
$592
Save $299
From PHL
Elite
Sep 11
Chicago, United States
69% AI deal score
$5,286
$3,277
Save $2,009
From PHL
Elite
Sep 27
Chicago, United States
69% AI deal score
$5,186
$3,333
Save $1,853
From PHL
Elite
Jun 30
Chicago, United States
69% AI deal score
$644
$547
Save $97
From PHL
Elite
Jul 01
Chicago, United States
68% AI deal score
$605
$544
Save $61
From PHL
Elite
Jul 01
Chicago, United States
67% AI deal score
$634
$562
Save $72
From PHL
Elite
Sep 23
Chicago, United States
67% AI deal score
$695
$559
Save $136
From PHL
Elite
Nov 05
Chicago, United States
66% AI deal score
$670
$600
Save $70
From PHL
Elite
Oct 09
Chicago, United States
65% AI deal score
$1,316
$1,019
Save $297
From PHL
Elite
Aug 21
Chicago, United States
50% AI deal score
$1,214
$901
Save $313
From PHL
Elite
Jul 21
Chicago, United States
50% AI deal score
$595
$559
Save $36
From PHL
Elite
Sep 26
Chicago, United States
50% AI deal score
$727
$654
Save $73
From PHL
Elite
Jun 16
Chicago, United States
49% AI deal score
$1,019
$873
Save $146
From PHL
Elite
Jul 08
Chicago, United States
49% AI deal score
$581
$559
Save $22
From PHL
Elite
Jul 29
Chicago, United States
49% AI deal score
$582
$559
Save $23
From PHL
Elite
Jul 15
Chicago, United States
49% AI deal score
$582
$559
Save $23
From PHL
Elite
Jul 22
Chicago, United States
49% AI deal score
$582
$559
Save $23
From PHL
Elite
Jul 22
Chicago, United States
47% AI deal score
$577
From PHL
Elite
Dec 10
Chicago, United States
47% AI deal score
$668
$600
Save $68
From PHL
Elite
Dec 02
Chicago, United States
47% AI deal score
$577
From PHL
Elite
Aug 21
Chicago, United States
47% AI deal score
$771
$661
Save $110
From PHL
Elite
Sep 16
Chicago, United States
46% AI deal score
$577
From PHL
Elite
Aug 12
Chicago, United States
46% AI deal score
$1,204
$1,049
Save $155
From PHL
Elite
Jul 31
Chicago, United States
45% AI deal score
$2,533
From PHL
Elite
Jul 02
Chicago, United States
45% AI deal score
$2,437
From PHL
Elite
Jun 30
Chicago, United States
43% AI deal score
$635
$633
Save $2
From PHL
Elite
Aug 09
Chicago, United States
43% AI deal score
$1,328
From PHL
Elite
Aug 09
Chicago, United States
43% AI deal score
$1,339
From PHL
Elite
Jul 02
Chicago, United States
43% AI deal score
$3,000
From PHL
Elite
Sep 02
Chicago, United States
42% AI deal score
$577
From PHL
Elite
Jul 19
Chicago, United States
42% AI deal score
$1,339
From PHL
Elite
Jun 20
Chicago, United States
42% AI deal score
$1,407
From PHL
Elite
Jun 19
Chicago, United States
42% AI deal score
$1,429
From PHL
Elite
Jun 18
Chicago, United States
42% AI deal score
$1,431
From PHL
Elite
Jun 19
Chicago, United States
42% AI deal score
$1,441
From PHL
Elite
Jun 18
Chicago, United States
42% AI deal score
$1,476
From PHL
Elite
Jun 17
Chicago, United States
42% AI deal score
$1,484
From PHL
Elite
Jun 21
Chicago, United States
41% AI deal score
$1,713
From PHL
Elite
Jun 22
Chicago, United States
41% AI deal score
$1,713
From PHL
Elite
Jun 16
Chicago, United States
41% AI deal score
$1,718
From PHL
Elite
Jun 17
Chicago, United States
41% AI deal score
$1,718
From PHL
Elite
Jun 22
Chicago, United States
41% AI deal score
$1,736
From PHL
Elite
Jun 21
Chicago, United States
41% AI deal score
$1,816
From PHL
Elite
Jul 14
Chicago, United States
40% AI deal score
$2,355
From PHL
Elite
Jul 14
Chicago, United States
40% AI deal score
$2,378
From PHL
Elite
Jul 27
Chicago, United States
40% AI deal score
$2,609
From PHL
Elite
Aug 10
Chicago, United States
40% AI deal score
$2,874
From PHL
Elite
Jul 08
Chicago, United States
39% AI deal score
$2,513
From PHL
Elite
Jul 08
Chicago, United States
39% AI deal score
$2,536
From PHL
Elite
Jul 27
Chicago, United States
39% AI deal score
$2,586
From PHL
Elite
Jul 09
Chicago, United States
39% AI deal score
$2,691
From PHL
Elite
Aug 05
Chicago, United States
39% AI deal score
$2,869
From PHL
Elite
Aug 08
Chicago, United States
39% AI deal score
$2,892
From PHL
Elite
Aug 09
Chicago, United States
39% AI deal score
$2,897
From PHL
Elite
Aug 07
Chicago, United States
39% AI deal score
$2,897
From PHL
Elite
Jul 09
Chicago, United States
38% AI deal score
$2,714
From PHL
Elite
Jul 14
Chicago, United States
38% AI deal score
$2,791
From PHL
Elite
Jul 31
Chicago, United States
38% AI deal score
$2,969
From PHL
Elite
Aug 02
Chicago, United States
38% AI deal score
$2,969
From PHL
Elite
Jul 14
Chicago, United States
38% AI deal score
$2,992
From PHL
Elite
Jul 08
Chicago, United States
38% AI deal score
$3,012
From PHL
Elite
Jul 14
Chicago, United States
37% AI deal score
$2,993
From PHL
Elite
Jul 14
Chicago, United States
37% AI deal score
$2,996
From PHL
Elite
Jun 16
Chicago, United States
36% AI deal score
$1,395
From PHL
Elite
Jun 18
Chicago, United States
36% AI deal score
$1,901
From PHL
Elite
Jun 16
Chicago, United States
35% AI deal score
$3,954
From PHL
Elite
Jun 16
Chicago, United States
34% AI deal score
$1,549
From PHL
Elite
Jul 18
Chicago, United States
31% AI deal score
$1,505
From PHL
Elite
Jun 16
Chicago, United States
31% AI deal score
$2,051
From PHL
Elite
Jun 19
Chicago, United States
31% AI deal score
$2,522
From PHL
Elite
Jun 17
Chicago, United States
31% AI deal score
$2,723
From PHL
Elite
Jul 08
Chicago, United States
31% AI deal score
$3,570
From PHL
Elite
Aug 27
Chicago, United States
31% AI deal score
$3,575
From PHL
Elite
Aug 26
Chicago, United States
31% AI deal score
$3,920
From PHL
Elite
Jul 10
Chicago, United States
31% AI deal score
$3,992