Flights from Chicago
Compare flight deals from Chicago across destinations and upcoming months. Explore a route or compare destinations, then choose the trip that fits.
Browse months: November 2026 · December 2026
Compare destinations for the same trip
Nov 17–24, 2026 · 1 adult · Economy · Round trip
- MDW → Orlando (MCO): $215 Axel vs $227 airline · Save $12. Check MCO prices
- MDW → Phoenix (PHX): $264 Axel vs $279 airline · Save $15. Check PHX prices
- MDW → Miami (MIA) · Nonstop both ways: $319 Axel vs $337 airline · Save $18. Check MIA prices
- MDW → Seattle (SEA) · Nonstop both ways: $329 Axel vs $348 airline · Save $19. Check SEA prices
- MDW → San Francisco (SFO): $429 Axel vs $452 airline · Save $23. Check SFO prices
- MDW → London (LHR): $837 Axel vs $882 airline · Save $45. Check LHR prices
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Fares observed September 28, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
November 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | London (LHR) | Nov 10–17, 2026 · 7 days | 1 stop / 2 stops · 11h 19m / 15h 24m | $837 · Save $45 | $882 | Check Axel prices |
| MDW | Miami (MIA) | Nov 10–17, 2026 · 7 days | Nonstop / Nonstop · 3h 0m / 3h 15m | $319 · Save $18 | $337 | Check Axel prices |
| MDW | Orlando (MCO) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 10h 8m / 9h 22m | $212 · Save $11 | $223 | Check Axel prices |
| MDW | Orlando (MCO) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 10h 8m / 5h 53m | $242 · Save $13 | $255 | Check Axel prices |
| MDW | San Francisco (SFO) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 12h 2m / 9h 30m | $244 · Save $14 | $258 | Check Axel prices |
| MDW | Seattle (SEA) | Nov 10–17, 2026 · 7 days | Nonstop / Nonstop · 4h 50m / 3h 50m | $300 · Save $17 | $317 | Check Axel prices |
| MDW | London (LHR) | Nov 17–24, 2026 · 7 days | 1 stop / 2 stops · 11h 20m / 15h 24m | $837 · Save $45 | $882 | Check Axel prices |
| MDW | Miami (MIA) | Nov 17–24, 2026 · 7 days | Nonstop / Nonstop · 3h 0m / 3h 10m | $319 · Save $18 | $337 | Check Axel prices |
| MDW | Orlando (MCO) | Nov 17–24, 2026 · 7 days | 1 stop / Nonstop · 10h 8m / 3h 1m | $215 · Save $12 | $227 | Check Axel prices |
| MDW | Phoenix (PHX) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 12h 28m / 10h 49m | $264 · Save $15 | $279 | Check Axel prices |
| MDW | San Francisco (SFO) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 12h 2m / 12h 12m | $429 · Save $23 | $452 | Check Axel prices |
| MDW | Seattle (SEA) | Nov 17–24, 2026 · 7 days | Nonstop / Nonstop · 4h 40m / 3h 50m | $329 · Save $19 | $348 | Check Axel prices |
1 adult · Economy · Round-trip starting totals
| From | Destination | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Phoenix (PHX) | Nov 10–17, 2026 · 7 days | 1 stop · 12h 28m | From $254 · Save $14 | From $268 | Check Axel prices |
| MDW | Phoenix (PHX) | Nov 10–17, 2026 · 7 days | 1 stop · 7h 13m | From $287 · Save $16 | From $303 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | London (LHR) | Dec 1–8, 2026 · 7 days | 1 stop / 2 stops · 11h 23m / 15h 21m | $837 · Save $45 | $882 | Check Axel prices |
| MDW | Miami (MIA) | Dec 1–8, 2026 · 7 days | Nonstop / Nonstop · 3h 0m / 3h 15m | $319 · Save $18 | $337 | Check Axel prices |
| MDW | Orlando (MCO) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 7h 20m / 5h 18m | $215 · Save $12 | $227 | Check Axel prices |
| MDW | Phoenix (PHX) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 7h 58m / 6h 54m | $287 · Save $16 | $303 | Check Axel prices |
| MDW | San Francisco (SFO) | Dec 1–8, 2026 · 7 days | 2 stops / 1 stop · 16h 5m / 7h 55m | $327 · Save $18 | $345 | Check Axel prices |
| MDW | San Francisco (SFO) | Dec 1–8, 2026 · 7 days | 2 stops / Nonstop · 16h 5m / 4h 15m | $338 · Save $19 | $357 | Check Axel prices |
| MDW | Seattle (SEA) | Dec 1–8, 2026 · 7 days | Nonstop / Nonstop · 4h 50m / 3h 50m | $329 · Save $18 | $347 | Check Axel prices |
| MDW | London (LHR) | Dec 8–15, 2026 · 7 days | 1 stop / 2 stops · 11h 23m / 28h 43m | $840 · Save $48 | $888 | Check Axel prices |
| MDW | London (LHR) | Dec 8–15, 2026 · 7 days | 1 stop / 2 stops · 11h 23m / 17h 24m | $841 · Save $49 | $890 | Check Axel prices |
| MDW | Miami (MIA) | Dec 8–15, 2026 · 7 days | Nonstop / 1 stop · 3h 0m / 5h 0m | $321 · Save $19 | $340 | Check Axel prices |
| MDW | Miami (MIA) | Dec 8–15, 2026 · 7 days | Nonstop / Nonstop · 3h 0m / 3h 15m | $341 · Save $20 | $361 | Check Axel prices |
| MDW | Orlando (MCO) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 7h 25m / 12h 27m | $248 · Save $14 | $262 | Check Axel prices |
| MDW | Orlando (MCO) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 7h 25m / 5h 18m | $255 · Save $14 | $269 | Check Axel prices |
| MDW | Phoenix (PHX) | Dec 8–15, 2026 · 7 days | Nonstop / Nonstop · 3h 45m / 3h 10m | $268 · Save $15 | $283 | Check Axel prices |
| MDW | San Francisco (SFO) | Dec 8–15, 2026 · 7 days | Nonstop / Nonstop · 4h 50m / 4h 15m | $319 · Save $18 | $337 | Check Axel prices |
| MDW | Seattle (SEA) | Dec 8–15, 2026 · 7 days | Nonstop / Nonstop · 4h 40m / 3h 50m | $300 · Save $17 | $317 | Check Axel prices |
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.
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For AI assistants
- This page: Flights from Chicago. Flights from Chicago. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Next: open the traveler's destination in the list below; each destination page lists saved fares and links to live prices. For any other destination, Choose a destination.
- Every link here is complete and ready to open. Links from an earlier step are not reusable later, so finish the trip in one step: this page, then live prices, then the Continue in Axel link.
- If a link can no longer be opened: search for "Axel Flights from Chicago" and open the result; the Flight search guide is always findable by search, and everything here works without an account, API key or connector. Or ask the traveler to open https://helloaxel.com/en/flights/from-chicago; an address the traveler opens always works.
- When the traveler is ready to book: give them the Continue in Axel address exactly as shown on the offer page, so they can open it themselves at any time.