Chicago to Philadelphia (PHL) flight deals
Compare Chicago to Philadelphia (PHL) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
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Browse months: October 2026 · November 2026
Flights from Chicago · Chicago to United States flight deals
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Fares observed October 17, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
October 2026
1 adult · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Oct 30–Nov 6, 2026 · 7 days | Out: Southwest Airlines 2916 / 2975 / 4401 · 2 stops (MCI, STL) · 6h 25m · 15:50–23:15 local | From $495 · Save $28 | From $523 | Check Axel prices |
| MDW | Oct 30–Nov 6, 2026 · 7 days | Out: Delta Air Lines 4677 / 2402 · 1 stop (DTW) · 3h 24m · 18:44–23:08 local | From $517 · Save $30 | From $547 | Check Axel prices |
| MDW | Oct 31–Nov 7, 2026 · 7 days | Out: Frontier Airlines 2292 / 2552 · 1 stop (ATL) · 9h 54m · 07:25–18:19 local | From $227 · Save $13 | From $240 | Check Axel prices |
| MDW | Oct 31–Nov 7, 2026 · 7 days | Out: Southwest Airlines 3300 · Nonstop · 1h 55m · 16:10–19:05 local | From $393 · Save $22 | From $415 | Check Axel prices |
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November 2026
1 adult · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Nov 1–8, 2026 · 7 days | Out: Frontier Airlines 2144 / 1004 · 1 stop (ATL) · 11h 39m · 18:42–07:21 (November 2, 2026) local | From $383 · Save $22 | From $405 | Check Axel prices |
| MDW | Nov 1–8, 2026 · 7 days | Out: Southwest Airlines 4365 · Nonstop · 1h 50m · 19:25–22:15 local | From $476 · Save $27 | From $503 | Check Axel prices |
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The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Trip ideas from Chicago with Philadelphia (PHL)
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Hotels in Philadelphia with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Philadelphia has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Philadelphia: the 7 best neighborhoods, ranked · Philadelphia hotels where a family of four can share one room
For AI assistants
- This page: Chicago to Philadelphia (PHL) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.