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Philadelphia to Chicago PHL, TTN → MDW, ORD

Philadelphia International Airport (PHL), Trenton-Mercer Airport (TTN) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD)

The cheapest return found recently is $255 with Frontier Airlines, 1 Nov – 6 Nov, found today. The cheapest one-way found recently is $135 with Frontier Airlines, 31 Oct, found 4 days ago.

Return

The cheapest return fare on each of 5 departure dates is usually $244 to $368.

Cheapest return found recently

$255

1 Nov – 6 Nov · Frontier Airlines

Philadelphia International Airport (PHL) → O'Hare International Airport (ORD)

Leaves 7:50 a.m. · Return leaves 4:42 p.m. · 11 h 9 min of travel, both ways together

out 1 stop, back nonstop

found today

See prices for these datesCheck today's price

Cheapest nonstop return

$368

15 Jul 2027 – 17 Jul 2027 · American Airlines

Philadelphia International Airport (PHL) → O'Hare International Airport (ORD)

Leaves 5:15 a.m. · Return leaves 5:00 a.m. · 4 h 28 min of travel, both ways together

out nonstop, back nonstop

found yesterday

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Found recently, and the cheapest we hold

Cheapest found recently $255 1 Nov – 6 Novfound todaySee prices for these dates

Cheapest we hold, of any age $191 13 Nov – 15 Novfound 6 days agoSee prices for these dates

What have prices looked like?

Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $131 to $244.

At $255, the cheapest return found recently is above that range.

25 days is a short history, so treat this range as an early guide.

Those were the prices on those days, not today's.

Is this a good return price?

Compared with the cheapest return fare on each of 5 departure dates from 20 Oct to 15 Jul 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.

Could nearby dates be cheaper?

We hold no other 5-night return fares leaving within 3 days of 1 Nov to compare.

Every date we hold

10 fares on 5 departure dates

20 Oct – 22 Oct: $495, found 3 days ago21 Oct – 24 Oct: $253, found 6 days ago1 Nov – 5 Nov: $244, found 3 days ago13 Nov – 15 Nov: $191, found 6 days ago15 Jul 2027 – 17 Jul 2027: $368, found yesterdayOctNovJul
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
20 Oct – 22 Oct$495Southwest AirlinesPhiladelphia International Airport (PHL) → Chicago Midway International Airport (MDW)out nonstop, back nonstopfound 3 days agoSee prices for these dates
21 Oct – 24 Oct$253Frontier AirlinesPhiladelphia International Airport (PHL) → Chicago Midway International Airport (MDW)out 1 stop, back nonstopfound 6 days agoSee prices for these dates
1 Nov – 5 Nov$244Frontier AirlinesPhiladelphia International Airport (PHL) → O'Hare International Airport (ORD)out 1 stop, back nonstopfound 3 days agoSee prices for these dates
13 Nov – 15 Nov$191Frontier AirlinesPhiladelphia International Airport (PHL) → O'Hare International Airport (ORD)out nonstop, back nonstopfound 6 days agoSee prices for these dates
15 Jul 2027 – 17 Jul 2027$368American AirlinesPhiladelphia International Airport (PHL) → O'Hare International Airport (ORD)out nonstop, back nonstopfound yesterdaySee prices for these dates

Which month looks cheapest?

November 2026 is the cheapest month — from $191.

October 2026From $2532 departure dates21 Oct – 24 Oct · found 6 days agoSee prices for these dates
November 2026From $191Cheapest seen2 departure dates13 Nov – 15 Nov · found 6 days agoSee prices for these dates
July 2027From $3681 departure date15 Jul 2027 – 17 Jul 2027 · found yesterdaySee prices for these dates

Airlines on the cheapest dates: Frontier Airlines, Southwest Airlines, American Airlines.

One-way

The cheapest one-way fare on each of 4 departure dates is usually $128 to $162.

Cheapest one-way found recently

$135

31 Oct · Frontier Airlines

Philadelphia International Airport (PHL) → O'Hare International Airport (ORD)

Leaves 12:36 p.m. · 6 h 40 min trip

1 stop

found 4 days ago

Open this tripCheck today's price

Cheapest nonstop one-way

$106

24 Oct · Frontier Airlines

Philadelphia International Airport (PHL) → O'Hare International Airport (ORD)

Leaves 9:09 p.m. · 2 h 30 min trip

nonstop

found 5 days ago

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Found recently, and the cheapest we hold

Cheapest found recently $135 31 Octfound 4 days agoOpen this trip

Cheapest we hold, of any age $106 24 Octfound 5 days agoOpen this trip

What have prices looked like?

Over 25 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $61 to $124.

At $135, the cheapest one-way found recently is above that range.

25 days is a short history, so treat this range as an early guide.

Those were the prices on those days, not today's.

Is this a good one-way price?

Compared with the cheapest one-way fare on each of 4 departure dates from 24 Oct to 31 Oct, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.

Could nearby dates be cheaper?

No. We hold one-way fares on 2 other departure dates within 3 days of 31 Oct, and none is cheaper.

Every date we hold

6 fares on 4 departure dates

24 Oct: $106, found 5 days ago28 Oct: $153, found 6 days ago30 Oct: $187, found 4 days ago31 Oct: $135, found 4 days agoOct
See the chart as a table
The cheapest price seen for each departure date — per traveler in Economy.
DatesFromAirlineAirportsStopsFound
24 Oct$106Frontier AirlinesPhiladelphia International Airport (PHL) → O'Hare International Airport (ORD)nonstopfound 5 days agoOpen this trip
28 Oct$153Frontier AirlinesPhiladelphia International Airport (PHL) → O'Hare International Airport (ORD)1 stopfound 6 days agoOpen this trip
30 Oct$187Frontier AirlinesTrenton-Mercer Airport (TTN) → O'Hare International Airport (ORD)1 stopfound 4 days agoOpen this trip
31 Oct$135Frontier AirlinesPhiladelphia International Airport (PHL) → O'Hare International Airport (ORD)1 stopfound 4 days agoOpen this trip

Airlines on the cheapest dates: Frontier Airlines.

Premium cabin fares from Philadelphia to Chicago

We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.

Today's prices for 1 Nov – 6 Nov in another cabin: Premium economy · Business · First

Today's prices for 31 Oct in another cabin: Premium economy · Business · First

How far ahead were prices cheapest for Philadelphia to Chicago?

Return

Fares 14 to 29 days before departure were typically 53% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 18 Oct (25 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

See these ranges as a table
Typical price in each booking range — round trip, per traveler in Economy.
Booked ahead byTypical fareCheapest dayAbove the cheapestDays of prices
0–6 days$281$234+115%23
7–13 days$262$223+100%19
14–29 days$131$131Cheapest seen11
90–179 days$197$166+50%24
180+ days$346$249+164%25

One-way

Fares 30 to 59 days before departure were typically 54% lower than 0 to 6 days before departure.

From the cheapest one-way each day between 24 Sept and 18 Oct (25 days), grouped by how many days ahead the flight left; one adult in economy.

Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.

Prices reflect recent searches — current fares may differ.

See these ranges as a table
Typical price in each booking range — one way, per traveler in Economy.
Booked ahead byTypical fareCheapest dayAbove the cheapestDays of prices
0–6 days$135$94+116%20
7–13 days$145$106+132%17
14–29 days$67$63+7%19
30–59 days$63$61Cheapest seen12
90–179 days$124$65+98%17

Could a nearby airport be cheaper?

A different airport at either end can change the fare — sometimes a lot.

Return

New York → Chicago

130 km from Philadelphia

$254

$1 less than flying from Philadelphia

4 Dec – 6 Dec · EWR → ORD · out nonstop, back nonstop

found yesterday

See this route

Baltimore → Chicago

145 km from Philadelphia

$240

$15 less than flying from Philadelphia

4 Nov – 7 Nov · BWI → MDW · out 1 stop, back 1 stop

found 2 days ago

See this route

Wilmington → Chicago

40 km from Philadelphia

$761

$506 more than flying from Philadelphia

1 Nov – 5 Nov · ILG → ORD · out 2 stops, back 2 stops

found 3 days ago

Check today's price

Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.

One-way

Baltimore → Chicago

145 km from Philadelphia

$117

$18 less than flying from Philadelphia

25 Nov · BWI → ORD · nonstop

found 3 days ago

See this route

New York → Chicago

130 km from Philadelphia

$164

$29 more than flying from Philadelphia

20 Dec · EWR → ORD · nonstop

found yesterday

See this route

Cheapest recent price on each route — one way, per traveler in Economy. Distances are in a straight line.

Live price for these dates

The cheapest return found recently is for 1 Nov – 6 Nov. A live search on this page shows what those dates cost now, for one adult in economy.

Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work