New York to Chicago (MDW) flight deals
Compare New York to Chicago (MDW) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
Fare examples by month
Round-trip totals · Economy · USD. Choose a month to see the dates.
| Month | Travelers / trip length | Axel Member | Airline fare |
|---|---|---|---|
| October 2026 | 1 adult · 7 days | $258–$282 | $287–$317 |
| November 2026 | 1 adult · 7 days | $248–$674 | $276–$753 |
| December 2026 | 1 adult · 7 days | $248–$1,215 | $276–$1,358 |
| January 2027 | 1 adult · 7 days | $292–$298 | $327–$332 |
| February 2027 | 1 adult · 7 days | $210 | $234 |
| March 2027 | 1 adult · 7–14 days | $220 | $245 |
Fares observed September 22 – 24, 2026. USD for the travelers shown. Search a trip for current prices.
October 2026
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| JFK | Oct 6–13, 2026 · 7 days | 1 stop / 1 stop · 5h 44m / 4h 56m | $280 · Save $32 | $312 | Check Axel prices |
| LGA | Oct 6–13, 2026 · 7 days | Nonstop / 1 stop · 2h 20m / 6h 35m | $270 · Save $32 | $302 | Check Axel prices |
| LGA | Oct 6–13, 2026 · 7 days | Nonstop / Nonstop · 2h 20m / 2h 5m | $282 · Save $35 | $317 | Check Axel prices |
| JFK | Oct 20–27, 2026 · 7 days | 1 stop / 1 stop · 6h 37m / 4h 56m | $273 · Save $34 | $307 | Check Axel prices |
| LGA | Oct 20–27, 2026 · 7 days | Nonstop / Nonstop · 2h 20m / 2h 5m | $258 · Save $29 | $287 | Check Axel prices |
November 2026
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| LGA | Nov 6–13, 2026 · 7 days | 1 stop / 1 stop · 7h 17m / 8h 45m | $248 · Save $28 | $276 | Check Axel prices |
| JFK | Nov 6–13, 2026 · 7 days | 1 stop / 1 stop · 6h 3m / 5h 29m | $674 · Save $79 | $753 | Check Axel prices |
| LGA | Nov 20–27, 2026 · 7 days | Nonstop / Nonstop · 2h 25m / 2h 5m | $258 · Save $29 | $287 | Check Axel prices |
| JFK | Nov 20–27, 2026 · 7 days | 1 stop / 1 stop · 6h 5m / 5h 17m | $625 · Save $72 | $697 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| JFK | Dec 6–13, 2026 · 7 days | 1 stop / 1 stop · 6h 51m / 6h 48m | $525 · Save $59 | $584 | Check Axel prices |
| JFK | Dec 6–13, 2026 · 7 days | 1 stop / 1 stop · 6h 51m / 5h 12m | $881 · Save $103 | $984 | Check Axel prices |
| LGA | Dec 6–13, 2026 · 7 days | 1 stop / 1 stop · 15h 12m / 24h 38m | $248 · Save $28 | $276 | Check Axel prices |
| JFK | Dec 20–27, 2026 · 7 days | 1 stop / 1 stop · 5h 44m / 5h 12m | $1,215 · Save $143 | $1,358 | Check Axel prices |
| LGA | Dec 20–27, 2026 · 7 days | 1 stop / 1 stop · 8h 2m / 25h 59m | $574 · Save $65 | $639 | Check Axel prices |
| LGA | Dec 20–27, 2026 · 7 days | 1 stop / 1 stop · 8h 2m / 6h 41m | $575 · Save $65 | $640 | Check Axel prices |
January 2027
1 adult · Economy · Round-trip totals
| From | Travel dates | Flights (out / return) | Axel Member | Airline fare | Search |
|---|---|---|---|---|---|
| JFK | Jan 6–13, 2027 · 7 days | 2 stops / 1 stop · 8h 15m / 4h 7m | $298 · Save $34 | $332 | Check Axel prices |
| JFK | Jan 20–27, 2027 · 7 days | 1 stop / 1 stop · 5h 21m / 4h 7m | $292 · Save $35 | $327 | Check Axel prices |
February 2027
Round-trip totals in USD for 1 adult · Economy · 7 days.
| From | Destination | Trip dates | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|
| EWR | Chicago (MDW) | Feb 24–Mar 3, 2027 | $210 · Save $24 | $234 | 1 stop | Check Axel prices |
March 2027
Round-trip totals in USD for 1 adult · Economy.
| From | Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|---|
| LGA | Chicago (MDW) | Mar 2–9, 2027 | 7 | $220 · Save $25 | $245 | 1 stop | Check Axel prices |
| LGA | Chicago (MDW) | Mar 2–16, 2027 | 14 | $220 · Save $25 | $245 | 1 stop | Check Axel prices |
Non-members can also book and save on airline fares. Live search shows prices with and without Membership. Optional Membership: $15 for the first month, then $10/month. Cancel anytime.
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