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Cheap flights Philadelphia — Chicago

Philadelphia (PHL, US) Chicago (MDW, US)
from $100 1 068 km ~1h 45m 15 flights found 2 airlines cheapest on Tuesday
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $100 on 15.12.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
Mo
Tu
We
Th
Fr
Sa
Su
December 2026
Mo
Tu
We
Th
Fr
Sa
Su
January 2027
Mo
Tu
We
Th
Fr
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Prices found for 3 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Cheapest flights found
15 Dec 2026, Tue
Southwest Airlines WN 2205
21:25
PHL Philadelphia International Airport
23:40
MDW Chicago Midway International Airport
2h 15m Direct
Farera
$100
View this ticket
16 Nov 2026, Mon
Frontier Airlines F9 1101
20:36
PHL Philadelphia International Airport
01:08
MDW Chicago Midway International Airport
4h 32m 1 stop
Farera
$178
View this ticket
15 Nov 2026, Sun
Frontier Airlines F9 1101
20:36
PHL Philadelphia International Airport
01:08
MDW Chicago Midway International Airport
4h 32m 1 stop
Farera
$181
View this ticket
15 Nov 2026, Sun
Southwest Airlines WN 1493
00:05
PHL Philadelphia International Airport
02:20
MDW Chicago Midway International Airport
2h 15m Direct
Farera
$203
View this ticket
16 Nov 2026, Mon
Southwest Airlines WN 2200
19:45
PHL Philadelphia International Airport
22:00
MDW Chicago Midway International Airport
2h 15m Direct
Farera
$245
View this ticket
15 Nov 2026, Sun
Southwest Airlines WN 3374
19:40
PHL Philadelphia International Airport
21:50
MDW Chicago Midway International Airport
2h 10m Direct
Tickets
$263
View this ticket
Route characteristics
Distance
1 068 km
Flight time
1h 45m
Time difference
-1h
Minimum price
from $100 (15.12.2026)
Average price
$153
Maximum price
$181
Departures per week
1
Cheapest day
Tuesday
Departure airports (1)
PHL Philadelphia International Airport
Arrival airports (1)
MDW Chicago Midway International Airport
Airlines (2)
WN Southwest Airlines F9 Frontier Airlines
Agencies (3)
Farera Kiwi.com Tickets
Prices by day of week
Monday
$178
avg $212
Tuesday
$100
avg $100
Cheapest
Sunday
$181
avg $216
Price trend by month
November 2026
from $178
avg $214
5 flights
December 2026
from $100
avg $100
1 flights
Airlines — cheapest prices 2
Southwest Airlines
Southwest Airlines
Low-cost 8 flights · 6 days
$100
Frontier Airlines
Frontier Airlines
Low-cost 7 flights · 6 days
$132
Where to buy tickets 3
Farera
10 tickets · 6 days
from $100
Kiwi.com
2 tickets · 2 days
from $154
Tickets
3 tickets · 2 days
from $263
Airports

From — Philadelphia (1)

  • PHL Philadelphia International Airport

To — Chicago (1)

  • MDW Chicago Midway International Airport
Other destinations from Philadelphia
Dallas
US · Hub
Miami
US · Hub
Seattle
US
Atlanta
US · Hub
Cincinnati
US
Memphis
US
Minneapolis
US · Hub
Salt Lake City
US
Cancun
MX
Denver
US · Hub
Punta Cana
DO
Frankfurt
DE · Hub
Frequently asked questions about the route Philadelphia — Chicago
How long is the flight from Philadelphia to Chicago?
Approximate flight time — 1h 45m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Philadelphia to Chicago?
The straight-line distance — 1 068 km.
How much do flights from Philadelphia to Chicago cost?
The minimum price over 3 months — from $100 on 15.12.2026.
What is the average ticket price?
The average price — $153. Range: $100 — $181.
What is the time difference between Philadelphia and Chicago?
The difference — -1h.
From which airports does Philadelphia operate flights?
From Philadelphia: PHL (Philadelphia International Airport).
To which airports in Chicago do flights arrive?
To Chicago: MDW (Chicago Midway International Airport).
Which airlines fly this route?
This route is served by 2 airlines: Southwest Airlines, Frontier Airlines.
Are there direct flights?
Yes, there are direct flights. Minimum direct price — from $100. Total direct flights found: 4.
Which day of the week is cheapest?
The cheapest day of the week — Tuesday.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route Philadelphia — Chicago

Flights Philadelphia — Chicago is a popular route. The straight-line distance is 1 068 km. Flight time 1h 45m. Time difference -1h.

From Philadelphia (PHL) flights depart from 1 airport: PHL. To Chicago (MDW) — 1 arrival airport: MDW.

2 airlines operate on this route: Southwest Airlines, Frontier Airlines.

The minimum price for the next 3 months — from $100 (15.12.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $153, ranging from $100 to $181. Book 1–3 months in advance to get the best deals.

Cheapest day to fly — Tuesday.

Other destinations in United States from Philadelphia
Dallas
US
Miami
US
Seattle
US
Atlanta
US
Cincinnati
US
Memphis
US
Minneapolis
US
Salt Lake City
US

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