Cheap flights from Philadelphia to Chicago
The cheapest round trip from Philadelphia to Chicago that travelers found recently is $301 with a carry-on: a $191 fare on Frontier plus about $110 for a carry-on both ways. It leaves Fri, Nov 13 and comes back Sun, Nov 15.
Live prices for Fri, Nov 13 to Sun, Nov 15
Cheapest trips travelers found recently
| Leave | Return | Airline | Airports | Stops | Fare | Carry-on (est.) | Total | Live prices |
|---|---|---|---|---|---|---|---|---|
| Fri, Nov 13 | Sun, Nov 15 | Frontier | PHL → ORD | Nonstop | $191 | +$110 | $301 | Live price |
| Mon, Mar 1 | Wed, Mar 3 | Frontier | PHL → ORD | 1 stop | $199 | +$110 | $309 | Live price |
| Thu, Oct 15 | Sat, Oct 17 | Frontier | PHL → ORD | Nonstop | $234 | +$110 | $344 | Live price |
| Thu, Jul 15 | Sat, Jul 17 | American Airlines | PHL → ORD | Nonstop | $347 | Included | $347 | Live price |
| Wed, Oct 21 | Sat, Oct 24 | Frontier | PHL → MDW | 1 stop | $253 | +$110 | $363 | Live price |
| Thu, Oct 22 | Sat, Oct 24 | Frontier | PHL → ORD | Nonstop | $262 | +$110 | $372 | Live price |
| Wed, Oct 21 | Fri, Oct 23 | Frontier | PHL → ORD | 1 stop | $297 | +$110 | $407 | Live price |
Round-trip prices per person, from real fares travelers found in the last few days. Carry-on fees are our estimate for each airline, both ways. Prices change fast: check the live price before you book.
Cheapest month to fly
| Month | Cheapest trip | From | Live prices |
|---|---|---|---|
| October 2026 | Thu, Oct 15 to Sat, Oct 17, 2 nights | $344 | Live price |
| November 2026 | Fri, Nov 13 to Sun, Nov 15, 2 nights | $301 | Live price |
| March 2027 | Mon, Mar 1 to Wed, Mar 3, 2 nights | $309 | Live price |
| July 2027 | Thu, Jul 15 to Sat, Jul 17, 2 nights | $347 | Live price |
Bag fees on this route
What the airlines flying Philadelphia to Chicago usually charge for one bag each way. Budget airlines often sell the cheapest fares and charge the most for bags, so compare the total, not the fare.
| Airline | Carry-on, each way | Checked bag, each way |
|---|---|---|
| American Airlines | Included | $40 |
| Frontier | $55 | $50 |
Our estimates: fees depend on the fare type and when you pay. Check the airline's own price when you book.
How these prices work
These are real round-trip fares that travelers found on Aviasales recently, not a live search, so they can change or sell out. Dipt adds an estimate of each airline's carry-on fee, so a cheap fare with expensive bags doesn't look cheaper than it is. "Live price" opens Dipt's live flight search for those dates, where you book with the airline or travel site you pick. Dipt may earn a commission when you book, at no extra cost to you (how Dipt makes money).
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