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Hartford → Chicago

Dec 11, 2026 · return Dec 16, 2026

BDL → MDW1 adulteconomyRound trip

5 flight options · 2 airlines

Nonstop flights

Fri, Dec 11 – Wed, Dec 16

Southwest Airlines
6:25 pmBDL
2h 30m
Nonstop
7:55 pmMDW
Southwest Airlines
1:20 pmMDW
2h 5m
Nonstop
4:25 pmBDL

Round-trip total · 1 adult · Taxes included

Fri, Dec 11 – Wed, Dec 16

Southwest Airlines
12:55 pmBDL
2h 30m
Nonstop
2:25 pmMDW
Southwest Airlines
1:20 pmMDW
2h 5m
Nonstop
4:25 pmBDL

Round-trip total · 1 adult · Taxes included

One-stop flights

Fri, Dec 11 – Wed, Dec 16

Delta Air Lines
5:17 amBDL
5h 29m
DTW · 1h 41m
9:46 amMDW
Delta Air Lines
9:30 amMDW
5h 52m
DTW · 2h 55m
4:22 pmBDL

Round-trip total · 1 adult · Taxes included

Fri, Dec 11 – Wed, Dec 16

Southwest Airlines
12:30 pmBDL
5h
BWI · 1h 35m
4:30 pmMDW
Southwest Airlines
1:20 pmMDW
2h 5m
Nonstop
4:25 pmBDL

Round-trip total · 1 adult · Taxes included

Fri, Dec 11 – Wed, Dec 16

Southwest Airlines
8:40 amBDL
5h 15m
BNA · 1h 10m
12:55 pmMDW
Southwest Airlines
1:20 pmMDW
2h 5m
Nonstop
4:25 pmBDL

Round-trip total · 1 adult · Taxes included

Make this trip yours

BDL ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeOct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 13, 2026 → Nov 16, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 11, 2026 → Dec 14, 2026Dec 12, 2026 → Dec 19, 2026Dec 22, 2026 → Dec 27, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Dec 30, 2026 → Jan 2, 2027Jan 8, 2027 → Jan 11, 2027Jan 9, 2027 → Jan 16, 2027Jan 15, 2027 → Jan 18, 2027Jan 22, 2027 → Jan 25, 2027Jan 23, 2027 → Jan 30, 2027Feb 5, 2027 → Feb 8, 2027Feb 6, 2027 → Feb 13, 2027Feb 12, 2027 → Feb 15, 2027Mar 5, 2027 → Mar 8, 2027Mar 6, 2027 → Mar 13, 2027Mar 25, 2027 → Mar 29, 2027Apr 2, 2027 → Apr 5, 2027Apr 3, 2027 → Apr 10, 2027Apr 30, 2027 → May 3, 2027May 1, 2027 → May 8, 2027May 28, 2027 → May 31, 2027May 29, 2027 → Jun 5, 2027Jun 25, 2027 → Jun 28, 2027Jun 26, 2027 → Jul 3, 2027Jul 2, 2027 → Jul 6, 2027Jul 23, 2027 → Jul 26, 2027Jul 24, 2027 → Jul 31, 2027Aug 20, 2027 → Aug 23, 2027Aug 21, 2027 → Aug 28, 2027Sep 3, 2027 → Sep 6, 2027Sep 17, 2027 → Sep 20, 2027Oct 30, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-11 → 2026-12-16Southwest AirlinesWN1668 / WN2757$300.002026-10-29T00:48:10Z
2026-12-11 → 2026-12-16Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814$380.002026-10-29T00:48:10Z
2026-12-11 → 2026-12-16Southwest AirlinesWN455 / WN2757$300.002026-10-29T00:48:10Z
2026-12-11 → 2026-12-16Southwest AirlinesWN449 + WN1071 / WN2757$315.002026-10-29T00:48:10Z
2026-12-11 → 2026-12-16Southwest AirlinesWN418 + WN1005 / WN2757$315.002026-10-29T00:48:10Z

2026-12-11 → 2026-12-16 · $300.00

  • Southwest Airlines WN1668: BDL 2026-12-11 18:25:00 → MDW 2026-12-11 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2757: MDW 2026-12-16 13:20:00 → BDL 2026-12-16 16:25:00; nonstop; 125 minutes. Local airport times.

2026-12-11 → 2026-12-16 · $380.00

  • Delta Air Lines DL2964 / DL4684: BDL 2026-12-11 05:17:00 → MDW 2026-12-11 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2026-12-11 05:17:00 → DTW 2026-12-11 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2026-12-11 09:10:00 → MDW 2026-12-11 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2026-12-16 09:30:00 → BDL 2026-12-16 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2026-12-16 09:30:00 → DTW 2026-12-16 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2026-12-16 14:40:00 → BDL 2026-12-16 16:22:00.

2026-12-11 → 2026-12-16 · $300.00

  • Southwest Airlines WN455: BDL 2026-12-11 12:55:00 → MDW 2026-12-11 14:25:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2757: MDW 2026-12-16 13:20:00 → BDL 2026-12-16 16:25:00; nonstop; 125 minutes. Local airport times.

2026-12-11 → 2026-12-16 · $315.00

  • Southwest Airlines WN449 / WN1071: BDL 2026-12-11 12:30:00 → MDW 2026-12-11 16:30:00; 1 stop(s) via BWI; 300 minutes. Local airport times.
    • WN449: BDL 2026-12-11 12:30:00 → BWI 2026-12-11 13:50:00; layover at BWI: 95 minutes.
    • WN1071: BWI 2026-12-11 15:25:00 → MDW 2026-12-11 16:30:00.
  • Southwest Airlines WN2757: MDW 2026-12-16 13:20:00 → BDL 2026-12-16 16:25:00; nonstop; 125 minutes. Local airport times.

2026-12-11 → 2026-12-16 · $315.00

  • Southwest Airlines WN418 / WN1005: BDL 2026-12-11 08:40:00 → MDW 2026-12-11 12:55:00; 1 stop(s) via BNA; 315 minutes. Local airport times.
    • WN418: BDL 2026-12-11 08:40:00 → BNA 2026-12-11 10:15:00; layover at BNA: 70 minutes.
    • WN1005: BNA 2026-12-11 11:25:00 → MDW 2026-12-11 12:55:00.
  • Southwest Airlines WN2757: MDW 2026-12-16 13:20:00 → BDL 2026-12-16 16:25:00; nonstop; 125 minutes. Local airport times.

More dates for this route