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Saint Louis → Chicago

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STL → MDW1 adulteconomy

72 flight options · 1 airline

Flights for the months ahead

Short round trips

  1. Thu, Nov 5 – Sun, Nov 8

    Southwest Airlines
    8:25 pmSTL
    1h 10m
    Nonstop
    9:35 pmMDW
    Southwest Airlines
    1:40 pmMDW
    1h 15m
    Nonstop
    2:55 pmSTL

    Round-trip total · 1 adult · Taxes included

  2. Fri, Nov 27 – Mon, Nov 30

    Southwest Airlines
    6:20 amSTL
    1h 5m
    Nonstop
    7:25 amMDW
    Southwest Airlines
    8:00 amMDW
    1h 25m
    Nonstop
    9:25 amSTL

    Round-trip total · 1 adult · Taxes included

  3. Fri, Dec 11 – Mon, Dec 14

    Southwest Airlines
    6:20 amSTL
    1h 5m
    Nonstop
    7:25 amMDW
    Southwest Airlines
    8:00 amMDW
    1h 25m
    Nonstop
    9:25 amSTL

    Round-trip total · 1 adult · Taxes included

  4. Thu, Dec 24 – Sun, Dec 27

    Southwest Airlines
    8:25 pmSTL
    1h 10m
    Nonstop
    9:35 pmMDW
    Southwest Airlines
    1:40 pmMDW
    1h 15m
    Nonstop
    2:55 pmSTL

    Round-trip total · 1 adult · Taxes included

  5. Fri, Feb 12 – Mon, Feb 15

    Southwest Airlines
    6:20 amSTL
    1h 5m
    Nonstop
    7:25 amMDW
    Southwest Airlines
    8:00 amMDW
    1h 25m
    Nonstop
    9:25 amSTL

    Round-trip total · 1 adult · Taxes included

  6. Fri, Apr 30 – Mon, May 3

    Southwest Airlines
    6:20 amSTL
    1h 5m
    Nonstop
    7:25 amMDW
    Southwest Airlines
    8:00 amMDW
    1h 25m
    Nonstop
    9:25 amSTL

    Round-trip total · 1 adult · Taxes included

  7. Fri, Jul 2 – Tue, Jul 6

    Southwest Airlines
    6:20 amSTL
    1h 5m
    Nonstop
    7:25 amMDW
    Southwest Airlines
    11:30 amMDW
    1h 10m
    Nonstop
    12:40 pmSTL

    Round-trip total · 1 adult · Taxes included

  8. Fri, Sep 17 – Mon, Sep 20

    Southwest Airlines
    6:20 amSTL
    1h 5m
    Nonstop
    7:25 amMDW
    Southwest Airlines
    8:00 amMDW
    1h 25m
    Nonstop
    9:25 amSTL

    Round-trip total · 1 adult · Taxes included

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1 of 8

Longer round trips

  1. Sat, Nov 14 – Sat, Nov 21

    Southwest Airlines
    5:30 amSTL
    1h 10m
    Nonstop
    6:40 amMDW
    Southwest Airlines
    7:50 amMDW
    1h 20m
    Nonstop
    9:10 amSTL

    Round-trip total · 1 adult · Taxes included

  2. Sat, Jan 2 – Sat, Jan 9

    Southwest Airlines
    5:30 amSTL
    1h 10m
    Nonstop
    6:40 amMDW
    Southwest Airlines
    7:50 amMDW
    1h 20m
    Nonstop
    9:10 amSTL

    Round-trip total · 1 adult · Taxes included

  3. Sat, Jan 16 – Sat, Jan 23

    Southwest Airlines
    5:30 amSTL
    1h 10m
    Nonstop
    6:40 amMDW
    Southwest Airlines
    7:50 amMDW
    1h 20m
    Nonstop
    9:10 amSTL

    Round-trip total · 1 adult · Taxes included

Swipe to see 2 more recent deals.

1 of 3

One-way flights

  1. Tue, Nov 10 · One way

    Southwest Airlines
    6:20 amSTL
    1h 5m
    Nonstop
    7:25 amMDW

    One-way total · 1 adult · Taxes included

Explore flights by month

Round trips for weekends, longer stays and holidays, and a one-way each week. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

November 2026

Nov 5 – Nov 8 · 3 nightsSouthwest AirlinesNonstop$260.00 Nov 6 – Nov 9 · 3 nightsSouthwest AirlinesNonstop$260.00 Nov 7 – Nov 14 · 7 nightsSouthwest AirlinesNonstop$260.00 Nov 10 · One waySouthwest AirlinesNonstop$135.00 Nov 12 – Nov 15 · 3 nightsSouthwest AirlinesNonstop$260.00 Nov 13 – Nov 16 · 3 nightsSouthwest AirlinesNonstop$260.00 Nov 14 – Nov 21 · 7 nightsSouthwest AirlinesNonstop$260.00 Nov 17 · One waySouthwest AirlinesNonstop$135.00 Nov 19 – Nov 22 · 3 nightsSouthwest AirlinesNonstop$260.00 Nov 20 – Nov 23 · 3 nightsSouthwest AirlinesNonstop$260.00 Nov 21 – Nov 28 · 7 nightsSouthwest AirlinesNonstop$299.00 Nov 24 · One waySouthwest AirlinesNonstop$175.50 Nov 24 – Nov 29 · 5 nightsSouthwest AirlinesNonstop$338.00 Nov 26 – Nov 29 · 3 nightsSouthwest AirlinesNonstop$338.00 Nov 27 – Nov 30 · 3 nightsSouthwest AirlinesNonstop$338.00 Nov 28 – Dec 5 · 7 nightsSouthwest AirlinesNonstop$299.00

December 2026

Dec 1 · One waySouthwest AirlinesNonstop$135.00 Dec 3 – Dec 6 · 3 nightsSouthwest AirlinesNonstop$260.00 Dec 4 – Dec 7 · 3 nightsSouthwest AirlinesNonstop$260.00 Dec 5 – Dec 12 · 7 nightsSouthwest AirlinesNonstop$260.00 Dec 8 · One waySouthwest AirlinesNonstop$135.00 Dec 10 – Dec 13 · 3 nightsSouthwest AirlinesNonstop$260.00 Dec 11 – Dec 14 · 3 nightsSouthwest AirlinesNonstop$260.00 Dec 12 – Dec 19 · 7 nightsSouthwest AirlinesNonstop$292.50 Dec 15 · One waySouthwest AirlinesNonstop$135.00 Dec 17 – Dec 20 · 3 nightsSouthwest AirlinesNonstop$292.50 Dec 18 – Dec 21 · 3 nightsSouthwest AirlinesNonstop$292.50 Dec 19 – Dec 26 · 7 nightsSouthwest AirlinesNonstop$325.00 Dec 22 · One waySouthwest AirlinesNonstop$168.75 Dec 22 – Dec 27 · 5 nightsSouthwest AirlinesNonstop$325.00 Dec 24 – Dec 27 · 3 nightsSouthwest AirlinesNonstop$325.00 Dec 25 – Dec 28 · 3 nightsSouthwest AirlinesNonstop$318.50 Dec 26 – Jan 2 · 7 nightsSouthwest AirlinesNonstop$318.50 Dec 29 · One waySouthwest AirlinesNonstop$162.00 Dec 30 – Jan 2 · 3 nightsSouthwest AirlinesNonstop$312.00 Dec 31 – Jan 3 · 3 nightsSouthwest AirlinesNonstop$312.00

January 2027

Jan 1 – Jan 4 · 3 nightsSouthwest AirlinesNonstop$286.00 Jan 2 – Jan 9 · 7 nightsSouthwest AirlinesNonstop$286.00 Jan 5 · One waySouthwest AirlinesNonstop$135.00 Jan 7 – Jan 10 · 3 nightsSouthwest AirlinesNonstop$260.00 Jan 8 – Jan 11 · 3 nightsSouthwest AirlinesNonstop$260.00 Jan 9 – Jan 16 · 7 nightsSouthwest AirlinesNonstop$260.00 Jan 12 · One waySouthwest AirlinesNonstop$135.00 Jan 14 – Jan 17 · 3 nightsSouthwest AirlinesNonstop$260.00 Jan 15 – Jan 18 · 3 nightsSouthwest AirlinesNonstop$260.00 Jan 16 – Jan 23 · 7 nightsSouthwest AirlinesNonstop$260.00 Jan 19 · One waySouthwest AirlinesNonstop$135.00 Jan 21 – Jan 24 · 3 nightsSouthwest AirlinesNonstop$260.00 Jan 22 – Jan 25 · 3 nightsSouthwest AirlinesNonstop$260.00 Jan 23 – Jan 30 · 7 nightsSouthwest AirlinesNonstop$260.00 Jan 26 · One waySouthwest AirlinesNonstop$135.00

Make this trip yours

STL ⇄ MDW

Economy

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

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More dates

Nov 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 2027
For AI assistants: every fare, every link, instructions

Saint Louis (STL) to Chicago (MDW), the months ahead: 72 priced flights on 72 exact dates. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Saint Louis (STL) to Chicago (MDW): November 2026

Travel datesAirlineStopsTotal price
Nov 5 – Nov 8 · 3 nightsSouthwest AirlinesNonstop$260.00
Nov 6 – Nov 9 · 3 nightsSouthwest AirlinesNonstop$260.00
Nov 7 – Nov 14 · 7 nightsSouthwest AirlinesNonstop$260.00
Nov 10 · One waySouthwest AirlinesNonstop$135.00
Nov 12 – Nov 15 · 3 nightsSouthwest AirlinesNonstop$260.00
Nov 13 – Nov 16 · 3 nightsSouthwest AirlinesNonstop$260.00
Nov 14 – Nov 21 · 7 nightsSouthwest AirlinesNonstop$260.00
Nov 17 · One waySouthwest AirlinesNonstop$135.00
Nov 19 – Nov 22 · 3 nightsSouthwest AirlinesNonstop$260.00
Nov 20 – Nov 23 · 3 nightsSouthwest AirlinesNonstop$260.00
Nov 21 – Nov 28 · 7 nightsSouthwest AirlinesNonstop$299.00
Nov 24 · One waySouthwest AirlinesNonstop$175.50
Nov 24 – Nov 29 · 5 nightsSouthwest AirlinesNonstop$338.00
Nov 26 – Nov 29 · 3 nightsSouthwest AirlinesNonstop$338.00
Nov 27 – Nov 30 · 3 nightsSouthwest AirlinesNonstop$338.00
Nov 28 – Dec 5 · 7 nightsSouthwest AirlinesNonstop$299.00

Saint Louis (STL) to Chicago (MDW): December 2026

Travel datesAirlineStopsTotal price
Dec 1 · One waySouthwest AirlinesNonstop$135.00
Dec 3 – Dec 6 · 3 nightsSouthwest AirlinesNonstop$260.00
Dec 4 – Dec 7 · 3 nightsSouthwest AirlinesNonstop$260.00
Dec 5 – Dec 12 · 7 nightsSouthwest AirlinesNonstop$260.00
Dec 8 · One waySouthwest AirlinesNonstop$135.00
Dec 10 – Dec 13 · 3 nightsSouthwest AirlinesNonstop$260.00
Dec 11 – Dec 14 · 3 nightsSouthwest AirlinesNonstop$260.00
Dec 12 – Dec 19 · 7 nightsSouthwest AirlinesNonstop$292.50
Dec 15 · One waySouthwest AirlinesNonstop$135.00
Dec 17 – Dec 20 · 3 nightsSouthwest AirlinesNonstop$292.50
Dec 18 – Dec 21 · 3 nightsSouthwest AirlinesNonstop$292.50
Dec 19 – Dec 26 · 7 nightsSouthwest AirlinesNonstop$325.00
Dec 22 · One waySouthwest AirlinesNonstop$168.75
Dec 22 – Dec 27 · 5 nightsSouthwest AirlinesNonstop$325.00
Dec 24 – Dec 27 · 3 nightsSouthwest AirlinesNonstop$325.00
Dec 25 – Dec 28 · 3 nightsSouthwest AirlinesNonstop$318.50
Dec 26 – Jan 2 · 7 nightsSouthwest AirlinesNonstop$318.50
Dec 29 · One waySouthwest AirlinesNonstop$162.00
Dec 30 – Jan 2 · 3 nightsSouthwest AirlinesNonstop$312.00
Dec 31 – Jan 3 · 3 nightsSouthwest AirlinesNonstop$312.00

Saint Louis (STL) to Chicago (MDW): January 2027

Travel datesAirlineStopsTotal price
Jan 1 – Jan 4 · 3 nightsSouthwest AirlinesNonstop$286.00
Jan 2 – Jan 9 · 7 nightsSouthwest AirlinesNonstop$286.00
Jan 5 · One waySouthwest AirlinesNonstop$135.00
Jan 7 – Jan 10 · 3 nightsSouthwest AirlinesNonstop$260.00
Jan 8 – Jan 11 · 3 nightsSouthwest AirlinesNonstop$260.00
Jan 9 – Jan 16 · 7 nightsSouthwest AirlinesNonstop$260.00
Jan 12 · One waySouthwest AirlinesNonstop$135.00
Jan 14 – Jan 17 · 3 nightsSouthwest AirlinesNonstop$260.00
Jan 15 – Jan 18 · 3 nightsSouthwest AirlinesNonstop$260.00
Jan 16 – Jan 23 · 7 nightsSouthwest AirlinesNonstop$260.00
Jan 19 · One waySouthwest AirlinesNonstop$135.00
Jan 21 – Jan 24 · 3 nightsSouthwest AirlinesNonstop$260.00
Jan 22 – Jan 25 · 3 nightsSouthwest AirlinesNonstop$260.00
Jan 23 – Jan 30 · 7 nightsSouthwest AirlinesNonstop$260.00
Jan 26 · One waySouthwest AirlinesNonstop$135.00

Saint Louis (STL) to Chicago (MDW): February 2027

Travel datesAirlineStopsTotal price
Feb 5 – Feb 8 · 3 nightsSouthwest AirlinesNonstop$260.00
Feb 6 – Feb 13 · 7 nightsSouthwest AirlinesNonstop$260.00
Feb 12 – Feb 15 · 3 nightsSouthwest AirlinesNonstop$260.00

Saint Louis (STL) to Chicago (MDW): March 2027

Travel datesAirlineStopsTotal price
Mar 5 – Mar 8 · 3 nightsSouthwest AirlinesNonstop$260.00
Mar 6 – Mar 13 · 7 nightsSouthwest AirlinesNonstop$260.00
Mar 25 – Mar 29 · 4 nightsSouthwest AirlinesNonstop$302.50

Saint Louis (STL) to Chicago (MDW): April 2027

Travel datesAirlineStopsTotal price
Apr 2 – Apr 5 · 3 nightsSouthwest AirlinesNonstop$290.00
Apr 3 – Apr 10 · 7 nightsSouthwest AirlinesNonstop$290.00
Apr 30 – May 3 · 3 nightsSouthwest AirlinesNonstop$290.00

Saint Louis (STL) to Chicago (MDW): May 2027

Travel datesAirlineStopsTotal price
May 1 – May 8 · 7 nightsSouthwest AirlinesNonstop$290.00
May 28 – May 31 · 3 nightsSouthwest AirlinesNonstop$333.50
May 29 – Jun 5 · 7 nightsSouthwest AirlinesNonstop$311.75

Saint Louis (STL) to Chicago (MDW): June 2027

Travel datesAirlineStopsTotal price
Jun 25 – Jun 28 · 3 nightsSouthwest AirlinesNonstop$290.00
Jun 26 – Jul 3 · 7 nightsSouthwest AirlinesNonstop$311.75

Saint Louis (STL) to Chicago (MDW): July 2027

Travel datesAirlineStopsTotal price
Jul 2 – Jul 6 · 4 nightsSouthwest AirlinesNonstop$333.50
Jul 23 – Jul 26 · 3 nightsSouthwest AirlinesNonstop$290.00
Jul 24 – Jul 31 · 7 nightsSouthwest AirlinesNonstop$290.00

Saint Louis (STL) to Chicago (MDW): August 2027

Travel datesAirlineStopsTotal price
Aug 20 – Aug 23 · 3 nightsSouthwest AirlinesNonstop$290.00
Aug 21 – Aug 28 · 7 nightsSouthwest AirlinesNonstop$290.00

Saint Louis (STL) to Chicago (MDW): September 2027

Travel datesAirlineStopsTotal price
Sep 3 – Sep 6 · 3 nightsSouthwest AirlinesNonstop$333.50
Sep 17 – Sep 20 · 3 nightsSouthwest AirlinesNonstop$290.00

2026-11-05 → 2026-11-08 · $260.00

  • Southwest Airlines WN4770: STL 2026-11-05 20:25:00 → MDW 2026-11-05 21:35:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN3092: MDW 2026-11-08 13:40:00 → STL 2026-11-08 14:55:00; nonstop; 75 minutes. Local airport times.

2026-11-10 · one way · $135.00

  • Southwest Airlines WN4173: STL 2026-11-10 06:20:00 → MDW 2026-11-10 07:25:00; nonstop; 65 minutes. Local airport times.

2026-11-14 → 2026-11-21 · $260.00

  • Southwest Airlines WN4173: STL 2026-11-14 05:30:00 → MDW 2026-11-14 06:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2026-11-21 07:50:00 → STL 2026-11-21 09:10:00; nonstop; 80 minutes. Local airport times.

2026-11-27 → 2026-11-30 · $338.00

  • Southwest Airlines WN4173: STL 2026-11-27 06:20:00 → MDW 2026-11-27 07:25:00; nonstop; 65 minutes. Local airport times.
  • Southwest Airlines WN3042: MDW 2026-11-30 08:00:00 → STL 2026-11-30 09:25:00; nonstop; 85 minutes. Local airport times.

2026-12-11 → 2026-12-14 · $260.00

  • Southwest Airlines WN4173: STL 2026-12-11 06:20:00 → MDW 2026-12-11 07:25:00; nonstop; 65 minutes. Local airport times.
  • Southwest Airlines WN3042: MDW 2026-12-14 08:00:00 → STL 2026-12-14 09:25:00; nonstop; 85 minutes. Local airport times.

2026-12-24 → 2026-12-27 · $325.00

  • Southwest Airlines WN4770: STL 2026-12-24 20:25:00 → MDW 2026-12-24 21:35:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN3092: MDW 2026-12-27 13:40:00 → STL 2026-12-27 14:55:00; nonstop; 75 minutes. Local airport times.

2027-01-02 → 2027-01-09 · $286.00

  • Southwest Airlines WN4173: STL 2027-01-02 05:30:00 → MDW 2027-01-02 06:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-01-09 07:50:00 → STL 2027-01-09 09:10:00; nonstop; 80 minutes. Local airport times.

2027-01-16 → 2027-01-23 · $260.00

  • Southwest Airlines WN4173: STL 2027-01-16 05:30:00 → MDW 2027-01-16 06:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-01-23 07:50:00 → STL 2027-01-23 09:10:00; nonstop; 80 minutes. Local airport times.

2027-02-12 → 2027-02-15 · $260.00

  • Southwest Airlines WN4173: STL 2027-02-12 06:20:00 → MDW 2027-02-12 07:25:00; nonstop; 65 minutes. Local airport times.
  • Southwest Airlines WN3042: MDW 2027-02-15 08:00:00 → STL 2027-02-15 09:25:00; nonstop; 85 minutes. Local airport times.

2027-04-30 → 2027-05-03 · $290.00

  • Southwest Airlines WN4173: STL 2027-04-30 06:20:00 → MDW 2027-04-30 07:25:00; nonstop; 65 minutes. Local airport times.
  • Southwest Airlines WN3042: MDW 2027-05-03 08:00:00 → STL 2027-05-03 09:25:00; nonstop; 85 minutes. Local airport times.

2027-07-02 → 2027-07-06 · $333.50

  • Southwest Airlines WN4173: STL 2027-07-02 06:20:00 → MDW 2027-07-02 07:25:00; nonstop; 65 minutes. Local airport times.
  • Southwest Airlines WN2737: MDW 2027-07-06 11:30:00 → STL 2027-07-06 12:40:00; nonstop; 70 minutes. Local airport times.

2027-09-17 → 2027-09-20 · $290.00

  • Southwest Airlines WN4173: STL 2027-09-17 06:20:00 → MDW 2027-09-17 07:25:00; nonstop; 65 minutes. Local airport times.
  • Southwest Airlines WN3042: MDW 2027-09-20 08:00:00 → STL 2027-09-20 09:25:00; nonstop; 85 minutes. Local airport times.

More dates for this route