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Route overview: Hartford to Chicago (MDW) flight deals

Hartford → Chicago

Jun 2, 2027 · choose your return date

BDL → MDW1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

June 2027

Jun 2, 2027 · One waySouthwest AirlinesNonstop$185.00 Jun 2, 2027 · One wayDelta Air LinesUp to 1 stop each way$230.00 Jun 2, 2027 – Jun 3, 2027 · 1 nightSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 3, 2027 · 1 nightDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 4, 2027 · 2 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 4, 2027 · 2 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 5, 2027 · 3 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 5, 2027 · 3 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 6, 2027 · 4 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 6, 2027 · 4 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 7, 2027 · 5 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 7, 2027 · 5 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 8, 2027 · 6 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 8, 2027 · 6 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 9, 2027 · 7 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 9, 2027 · 7 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 10, 2027 · 8 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 10, 2027 · 8 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 11, 2027 · 9 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 11, 2027 · 9 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 12, 2027 · 10 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 12, 2027 · 10 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 13, 2027 · 11 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 13, 2027 · 11 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 14, 2027 · 12 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 14, 2027 · 12 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 15, 2027 · 13 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 15, 2027 · 13 nightsDelta Air LinesUp to 1 stop each way$430.00 Jun 2, 2027 – Jun 16, 2027 · 14 nightsSouthwest AirlinesNonstop$350.00 Jun 2, 2027 – Jun 16, 2027 · 14 nightsDelta Air LinesUp to 1 stop each way$430.00

Flights for your trip

  1. Wed, Jun 2 · One way

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  2. Wed, Jun 2 · One way

    Delta Air Lines
    5:17 amBDL
    5h 29m
    DTW · 1h 41m
    9:46 amMDW

    One-way total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  3. Wed, Jun 2 – Thu, Jun 3

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:20 pmMDW
    2h 5m
    Nonstop
    9:25 pmBDL

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  4. Wed, Jun 2 – Thu, Jun 3

    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

    Availability is checked when you select these flights.

  5. Wed, Jun 2 – Fri, Jun 4

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:20 pmMDW
    2h 5m
    Nonstop
    9:25 pmBDL

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  6. Wed, Jun 2 – Fri, Jun 4

    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

    Availability is checked when you select these flights.

  7. Wed, Jun 2 – Sat, Jun 5

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:45 pmMDW
    2h 5m
    Nonstop
    9:50 pmBDL

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  8. Wed, Jun 2 – Sat, Jun 5

    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

    Availability is checked when you select these flights.

  9. Wed, Jun 2 – Sun, Jun 6

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    7:50 amMDW
    2h
    Nonstop
    10:50 amBDL

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  10. Wed, Jun 2 – Sun, Jun 6

    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

    Availability is checked when you select these flights.

  11. Wed, Jun 2 – Tue, Jun 8

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:20 pmMDW
    2h 5m
    Nonstop
    9:25 pmBDL

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  12. Wed, Jun 2 – Tue, Jun 8

    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

    Availability is checked when you select these flights.

  13. Wed, Jun 2 – Wed, Jun 9

    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

    Availability is checked when you select these flights.

  14. Wed, Jun 2 – Wed, Jun 9

    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

    Availability is checked when you select these flights.

  15. Wed, Jun 2 – Thu, Jun 10

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:20 pmMDW
    2h 5m
    Nonstop
    9:25 pmBDL

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  16. Wed, Jun 2 – Thu, Jun 10

    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

    Availability is checked when you select these flights.

  17. Wed, Jun 2 – Sat, Jun 12

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:45 pmMDW
    2h 5m
    Nonstop
    9:50 pmBDL

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  18. Wed, Jun 2 – Sat, Jun 12

    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

    Availability is checked when you select these flights.

  19. Wed, Jun 2 – Sun, Jun 13

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    7:50 amMDW
    2h
    Nonstop
    10:50 amBDL

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  20. Wed, Jun 2 – Sun, Jun 13

    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

    Availability is checked when you select these flights.

  21. Wed, Jun 2 – Mon, Jun 14

    Southwest Airlines
    6:25 pmBDL
    2h 30m
    Nonstop
    7:55 pmMDW
    Southwest Airlines
    6:20 pmMDW
    2h 5m
    Nonstop
    9:25 pmBDL

    Round-trip total · 1 adult · Taxes included

    Availability is checked when you select these flights.

  22. Wed, Jun 2 – Mon, Jun 14

    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

    Availability is checked when you select these flights.

  23. Wed, Jun 2 – Wed, Jun 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

    Availability is checked when you select these flights.

  24. Wed, Jun 2 – Wed, Jun 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

    Availability is checked when you select these flights.

Swipe to see 23 more recent deals.

1 of 24

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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Explore this route

All dates for this routeJun 1, 2027 · Return optionsJun 3, 2027 · Return optionsHotels in Chicago with Axel
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Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown. To book or select flights, follow that row's price link; it keeps the exact dates and travelers.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-06-02 · one waySouthwest AirlinesWN1668Axel-exclusive $185.002026-10-29T00:48:10Z
2027-06-02 · one wayDelta Air LinesDL2964 + DL4684Axel-exclusive $230.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-03Southwest AirlinesWN1668 / WN1601Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-03Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-04Southwest AirlinesWN1668 / WN1601Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-04Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-05Southwest AirlinesWN1668 / WN4107Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-05Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-06Southwest AirlinesWN1668 / WN449Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-06Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-07Southwest AirlinesWN1668 / WN1601Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-07Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-08Southwest AirlinesWN1668 / WN1601Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-08Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-09Southwest AirlinesWN1668 / WN2757Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-09Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-10Southwest AirlinesWN1668 / WN1601Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-10Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-11Southwest AirlinesWN1668 / WN1601Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-11Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-12Southwest AirlinesWN1668 / WN4107Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-12Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-13Southwest AirlinesWN1668 / WN449Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-13Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-14Southwest AirlinesWN1668 / WN1601Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-14Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-15Southwest AirlinesWN1668 / WN1601Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-15Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-16Southwest AirlinesWN1668 / WN2757Axel-exclusive $350.002026-10-29T00:48:10Z
2027-06-02 → 2027-06-16Delta Air LinesDL2964 + DL4684 / DL4711 + DL2814Axel-exclusive $430.002026-10-29T00:48:10Z

Route overview: Hartford to Chicago (MDW) flight deals

2027-06-02 · one way · Axel-exclusive $185.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.

2027-06-02 · one way · Axel-exclusive $230.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.

2027-06-02 → 2027-06-03 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN1601: MDW 2027-06-03 18:20:00 → BDL 2027-06-03 21:25:00; nonstop; 125 minutes. Local airport times.

2027-06-02 → 2027-06-03 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-03 09:30:00 → BDL 2027-06-03 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-03 09:30:00 → DTW 2027-06-03 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-03 14:40:00 → BDL 2027-06-03 16:22:00.

2027-06-02 → 2027-06-04 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN1601: MDW 2027-06-04 18:20:00 → BDL 2027-06-04 21:25:00; nonstop; 125 minutes. Local airport times.

2027-06-02 → 2027-06-04 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-04 09:30:00 → BDL 2027-06-04 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-04 09:30:00 → DTW 2027-06-04 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-04 14:40:00 → BDL 2027-06-04 16:22:00.

2027-06-02 → 2027-06-05 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN4107: MDW 2027-06-05 18:45:00 → BDL 2027-06-05 21:50:00; nonstop; 125 minutes. Local airport times.

2027-06-02 → 2027-06-05 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-05 09:30:00 → BDL 2027-06-05 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-05 09:30:00 → DTW 2027-06-05 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-05 14:40:00 → BDL 2027-06-05 16:22:00.

2027-06-02 → 2027-06-06 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN449: MDW 2027-06-06 07:50:00 → BDL 2027-06-06 10:50:00; nonstop; 120 minutes. Local airport times.

2027-06-02 → 2027-06-06 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-06 09:30:00 → BDL 2027-06-06 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-06 09:30:00 → DTW 2027-06-06 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-06 14:40:00 → BDL 2027-06-06 16:22:00.

2027-06-02 → 2027-06-08 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN1601: MDW 2027-06-08 18:20:00 → BDL 2027-06-08 21:25:00; nonstop; 125 minutes. Local airport times.

2027-06-02 → 2027-06-08 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-08 09:30:00 → BDL 2027-06-08 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-08 09:30:00 → DTW 2027-06-08 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-08 14:40:00 → BDL 2027-06-08 16:22:00.

2027-06-02 → 2027-06-09 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2757: MDW 2027-06-09 13:20:00 → BDL 2027-06-09 16:25:00; nonstop; 125 minutes. Local airport times.

2027-06-02 → 2027-06-09 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-09 09:30:00 → BDL 2027-06-09 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-09 09:30:00 → DTW 2027-06-09 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-09 14:40:00 → BDL 2027-06-09 16:22:00.

2027-06-02 → 2027-06-10 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN1601: MDW 2027-06-10 18:20:00 → BDL 2027-06-10 21:25:00; nonstop; 125 minutes. Local airport times.

2027-06-02 → 2027-06-10 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-10 09:30:00 → BDL 2027-06-10 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-10 09:30:00 → DTW 2027-06-10 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-10 14:40:00 → BDL 2027-06-10 16:22:00.

2027-06-02 → 2027-06-12 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN4107: MDW 2027-06-12 18:45:00 → BDL 2027-06-12 21:50:00; nonstop; 125 minutes. Local airport times.

2027-06-02 → 2027-06-12 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-12 09:30:00 → BDL 2027-06-12 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-12 09:30:00 → DTW 2027-06-12 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-12 14:40:00 → BDL 2027-06-12 16:22:00.

2027-06-02 → 2027-06-13 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN449: MDW 2027-06-13 07:50:00 → BDL 2027-06-13 10:50:00; nonstop; 120 minutes. Local airport times.

2027-06-02 → 2027-06-13 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-13 09:30:00 → BDL 2027-06-13 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-13 09:30:00 → DTW 2027-06-13 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-13 14:40:00 → BDL 2027-06-13 16:22:00.

2027-06-02 → 2027-06-14 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN1601: MDW 2027-06-14 18:20:00 → BDL 2027-06-14 21:25:00; nonstop; 125 minutes. Local airport times.

2027-06-02 → 2027-06-14 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-14 09:30:00 → BDL 2027-06-14 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-14 09:30:00 → DTW 2027-06-14 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-14 14:40:00 → BDL 2027-06-14 16:22:00.

2027-06-02 → 2027-06-16 · Axel-exclusive $350.00

  • Southwest Airlines WN1668: BDL 2027-06-02 18:25:00 → MDW 2027-06-02 19:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2757: MDW 2027-06-16 13:20:00 → BDL 2027-06-16 16:25:00; nonstop; 125 minutes. Local airport times.

2027-06-02 → 2027-06-16 · Axel-exclusive $430.00

  • Delta Air Lines DL2964 / DL4684: BDL 2027-06-02 05:17:00 → MDW 2027-06-02 09:46:00; 1 stop(s) via DTW; 329 minutes. Local airport times.
    • DL2964: BDL 2027-06-02 05:17:00 → DTW 2027-06-02 07:29:00; layover at DTW: 101 minutes.
    • DL4684: DTW 2027-06-02 09:10:00 → MDW 2027-06-02 09:46:00.
  • Delta Air Lines DL4711 / DL2814: MDW 2027-06-16 09:30:00 → BDL 2027-06-16 16:22:00; 1 stop(s) via DTW; 352 minutes. Local airport times.
    • DL4711: MDW 2027-06-16 09:30:00 → DTW 2027-06-16 11:45:00; layover at DTW: 175 minutes.
    • DL2814: DTW 2027-06-16 14:40:00 → BDL 2027-06-16 16:22:00.

Explore this route

For AI assistants

  • This page: Hartford (BDL) to Chicago (MDW) · Jun 2, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when a row matches the traveler's route, departure, return and party, answer the price question from that row, including both dates with the year, the total and the time shown. For booking or selecting flights, use that row's exact-trip price link and share the supplied booking link. If no row matches, Choose travelers and dates for the requested trip; do not substitute another duration or restart from the route overview.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Hartford to Chicago (MDW) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.