Cheap flights from Philadelphia to Chicago from $143 PHL, TTN → MDW, ORD, RFD

Found recently, and the cheapest we hold

It is also the cheapest return we hold, of any age.

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest return we saw each day was $112 to $244.

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

Could nearby dates be cheaper?

We hold no other 7-night return fares leaving within 3 days of 5 Jan 2027 to compare.

Every date we hold

116 fares on 7 departure dates

Which month looks cheapest?

January 2027 is the cheapest month — from $180.

Found recently, and the cheapest we hold

It is also the cheapest one-way we hold, of any age.

What have prices looked like?

Over 49 days, 24 Sept to 11 Nov, the cheapest one-way we saw each day was $19 to $141.

At $143, the cheapest one-way found recently is above that range.

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

Could nearby dates be cheaper?

No. We hold one-way fares on 1 other departure date within 3 days of 21 Nov, and it is not cheaper.

Every date we hold

3 fares on 3 departure dates

Which month looks cheapest?

November 2026 is the cheapest month — from $143.

Return

Fares 14 to 29 days before departure were typically 52% lower than 0 to 6 days before departure.

From the cheapest return each day between 24 Sept and 11 Nov (49 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.

One-way

Fares 30 to 59 days before departure were typically 56% lower than 0 to 6 days before departure.

From the cheapest one-way each day between 24 Sept and 11 Nov (49 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.

How much is a return flight from Philadelphia to Chicago?

The cheapest return found recently is $180 with Frontier Airlines, 5 Jan 2027 to 12 Jan 2027, found 2 days ago. The cheapest return fare on each of 7 departure dates is usually $237 to $356.

How much is a one-way flight from Philadelphia to Chicago?

The cheapest one-way found recently is $143 with Frontier Airlines, 21 Nov, found 2 days ago. The cheapest one-way fare on each of 3 departure dates is usually $150 to $166.

What is the cheapest month to fly from Philadelphia to Chicago?

January 2027 is the cheapest month for a return, from $180, 5 Jan 2027 to 12 Jan 2027, found 2 days ago. November 2026 is the cheapest month for a one-way, from $143, 21 Nov, found 2 days ago.

How far ahead should I book a flight from Philadelphia to Chicago?

In 49 days of prices between 24 Sept and 11 Nov, return fares 14 to 29 days before departure were typically 52% lower than 0 to 6 days before departure. One-way fares 30 to 59 days before departure were typically 56% lower than 0 to 6 days before departure.

Is there a direct flight from Philadelphia to Chicago?

Yes, the cheapest nonstop return found recently is $196 with Southwest Airlines, 5 Jan 2027 to 12 Jan 2027, found 2 days ago. The cheapest nonstop one-way found recently is $157 with American Airlines, 9 Jun 2027, found 3 days ago.

How long is the flight from Philadelphia to Chicago?

The cheapest nonstop one-way found recently, with American Airlines on 9 Jun 2027, takes 2 h 29 min from Philadelphia International Airport (PHL) to O'Hare International Airport (ORD). The cheapest one-way found recently, with Frontier Airlines on 21 Nov, takes 27 h 51 min with 1 stop.

Which airlines have the cheapest flights from Philadelphia to Chicago?

Between 14 Nov and 15 Jul 2027, Frontier Airlines has the cheapest return on 5 of the 7 departure dates we hold, and American Airlines on 2. Between 20 Nov and 9 Jun 2027, Frontier Airlines has the cheapest one-way on 2 of the 3 departure dates we hold, and American Airlines on 1.