Chicago to Miami, Fort Lauderdale or Orlando flight deals
Compare flights from Chicago to Miami, Fort Lauderdale or Orlando across upcoming months. Explore the dated fares below, or search your own trip.
Browse months: November 2026 · December 2026
Compare destinations for the same trip
Nov 10–17, 2026 · 1 adult · Economy · Round trip
- MDW → Fort Lauderdale (FLL): $155 Axel vs $164 airline · Save $9. Check FLL prices
- ORD → Fort Lauderdale (FLL): $155 Axel vs $164 airline · Save $9. Check FLL prices
- ORD → Orlando (MCO): $165 Axel vs $175 airline · Save $10. Check MCO prices
- MDW → Orlando (MCO): $212 Axel vs $223 airline · Save $11. Check MCO prices
- ORD → Miami (MIA): $225 Axel vs $238 airline · Save $13. Check MIA prices
- MDW → Miami (MIA) · Nonstop both ways: $319 Axel vs $337 airline · Save $18. Check MIA prices
Flights from Chicago · Chicago to Florida flight deals · Chicago to United States flight deals
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Fares observed September 28, 2026. USD for the travelers shown. Search a trip for current prices.
November 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Fort Lauderdale (FLL) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 59m / 12h 8m | $155 · Save $9 | $164 | Check Axel prices |
| MDW | Fort Lauderdale (FLL) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 59m / 9h 32m | $192 · Save $11 | $203 | Check Axel prices |
| ORD | Fort Lauderdale (FLL) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 6h 0m / 7h 12m | $155 · Save $9 | $164 | Check Axel prices |
| ORD | Miami (MIA) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 17h 14m / 8h 46m | $225 · Save $13 | $238 | 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 |
| ORD | Orlando (MCO) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 11h 42m / 6h 47m | $165 · Save $10 | $175 | Check Axel prices |
| ORD | Orlando (MCO) | Nov 10–17, 2026 · 7 days | 1 stop / Nonstop · 11h 42m / 3h 15m | $224 · Save $13 | $237 | Check Axel prices |
| MDW | Fort Lauderdale (FLL) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 6h 59m / 10h 10m | $210 · Save $11 | $221 | Check Axel prices |
| MDW | Fort Lauderdale (FLL) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 6h 59m / 8h 23m | $277 · Save $15 | $292 | Check Axel prices |
| ORD | Fort Lauderdale (FLL) | Nov 17–24, 2026 · 7 days | 1 stop / Nonstop · 6h 0m / 3h 32m | $142 · Save $8 | $150 | Check Axel prices |
| ORD | Miami (MIA) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 17h 14m / 7h 51m | $254 · Save $14 | $268 | Check Axel prices |
| ORD | Miami (MIA) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 17h 14m / 6h 44m | $301 · Save $17 | $318 | 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 |
| ORD | Orlando (MCO) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 9h 9m / 10h 20m | $215 · Save $12 | $227 | Check Axel prices |
| ORD | Orlando (MCO) | Nov 17–24, 2026 · 7 days | 1 stop / Nonstop · 9h 9m / 3h 9m | $224 · Save $13 | $237 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Fort Lauderdale (FLL) | Dec 1–8, 2026 · 7 days | Nonstop / Nonstop · 3h 0m / 3h 5m | $173 · Save $10 | $183 | Check Axel prices |
| ORD | Fort Lauderdale (FLL) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 11h 22m / 10h 51m | $155 · Save $9 | $164 | 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 |
| ORD | Miami (MIA) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 5h 19m / 12h 27m | $215 · Save $12 | $227 | 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 |
| ORD | Orlando (MCO) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 11h 33m / 12h 22m | $205 · Save $12 | $217 | Check Axel prices |
| ORD | Orlando (MCO) | Dec 1–8, 2026 · 7 days | 1 stop / Nonstop · 11h 33m / 3h 11m | $236 · Save $13 | $249 | Check Axel prices |
| MDW | Fort Lauderdale (FLL) | Dec 8–15, 2026 · 7 days | Nonstop / 2 stops · 2h 55m / 8h 50m | $189 · Save $10 | $199 | Check Axel prices |
| MDW | Fort Lauderdale (FLL) | Dec 8–15, 2026 · 7 days | Nonstop / Nonstop · 2h 55m / 3h 5m | $360 · Save $20 | $380 | Check Axel prices |
| ORD | Fort Lauderdale (FLL) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 11h 31m / 10h 51m | $167 · Save $9 | $176 | 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 |
| ORD | Miami (MIA) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 5h 21m / 12h 27m | $215 · Save $12 | $227 | 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 |
| ORD | Orlando (MCO) | Dec 8–15, 2026 · 7 days | Nonstop / 1 stop · 2h 54m / 10h 22m | $205 · Save $12 | $217 | Check Axel prices |
| ORD | Orlando (MCO) | Dec 8–15, 2026 · 7 days | Nonstop / Nonstop · 2h 54m / 3h 11m | $244 · Save $14 | $258 | 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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