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Omaha → Chicago

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OMA → MDW1 adulteconomy

40 flight options · 1 airline

Flights for the months ahead

Short round trips

  1. Fri, Oct 30 – Mon, Nov 2

    Southwest Airlines
    1:35 pmOMA
    1h 25m
    Nonstop
    3:00 pmMDW
    Southwest Airlines
    10:05 amMDW
    1h 35m
    Nonstop
    11:40 amOMA

    Round-trip total · 1 adult · Taxes included

  2. Fri, Dec 11 – Mon, Dec 14

    Southwest Airlines
    1:35 pmOMA
    1h 25m
    Nonstop
    3:00 pmMDW
    Southwest Airlines
    10:05 amMDW
    1h 35m
    Nonstop
    11:40 amOMA

    Round-trip total · 1 adult · Taxes included

  3. Fri, Jan 15 – Mon, Jan 18

    Southwest Airlines
    1:35 pmOMA
    1h 25m
    Nonstop
    3:00 pmMDW
    Southwest Airlines
    10:05 amMDW
    1h 35m
    Nonstop
    11:40 amOMA

    Round-trip total · 1 adult · Taxes included

  4. Fri, Apr 30 – Mon, May 3

    Southwest Airlines
    1:35 pmOMA
    1h 25m
    Nonstop
    3:00 pmMDW
    Southwest Airlines
    10:05 amMDW
    1h 35m
    Nonstop
    11:40 amOMA

    Round-trip total · 1 adult · Taxes included

  5. Fri, Jun 25 – Mon, Jun 28

    Southwest Airlines
    1:35 pmOMA
    1h 25m
    Nonstop
    3:00 pmMDW
    Southwest Airlines
    10:05 amMDW
    1h 35m
    Nonstop
    11:40 amOMA

    Round-trip total · 1 adult · Taxes included

  6. Fri, Sep 17 – Mon, Sep 20

    Southwest Airlines
    1:35 pmOMA
    1h 25m
    Nonstop
    3:00 pmMDW
    Southwest Airlines
    10:05 amMDW
    1h 35m
    Nonstop
    11:40 amOMA

    Round-trip total · 1 adult · Taxes included

Swipe to see 5 more recent deals.

1 of 6

Longer round trips

  1. Sat, Nov 14 – Sat, Nov 21

    Southwest Airlines
    10:35 amOMA
    1h 25m
    Nonstop
    12:00 pmMDW
    Southwest Airlines
    9:25 pmMDW
    1h 40m
    Nonstop
    11:05 pmOMA

    Round-trip total · 1 adult · Taxes included

  2. Sat, Dec 26 – Sat, Jan 2

    Southwest Airlines
    10:35 amOMA
    1h 25m
    Nonstop
    12:00 pmMDW
    Southwest Airlines
    9:25 pmMDW
    1h 40m
    Nonstop
    11:05 pmOMA

    Round-trip total · 1 adult · Taxes included

  3. Sat, Feb 6 – Sat, Feb 13

    Southwest Airlines
    10:35 amOMA
    1h 25m
    Nonstop
    12:00 pmMDW
    Southwest Airlines
    9:25 pmMDW
    1h 40m
    Nonstop
    11:05 pmOMA

    Round-trip total · 1 adult · Taxes included

  4. Sat, Mar 6 – Sat, Mar 13

    Southwest Airlines
    10:35 amOMA
    1h 25m
    Nonstop
    12:00 pmMDW
    Southwest Airlines
    9:25 pmMDW
    1h 40m
    Nonstop
    11:05 pmOMA

    Round-trip total · 1 adult · Taxes included

  5. Sat, Jul 24 – Sat, Jul 31

    Southwest Airlines
    10:35 amOMA
    1h 25m
    Nonstop
    12:00 pmMDW
    Southwest Airlines
    9:25 pmMDW
    1h 40m
    Nonstop
    11:05 pmOMA

    Round-trip total · 1 adult · Taxes included

Swipe to see 4 more recent deals.

1 of 5

One-way flights

  1. Fri, Oct 30 · One way

    Southwest Airlines
    1:35 pmOMA
    1h 25m
    Nonstop
    3:00 pmMDW

    One-way total · 1 adult · Taxes included

Explore flights by month

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

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OMA ⇄ MDW

Economy

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

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More dates

Oct 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.

October 2026

Travel datesAirlineStopsTotal price
Oct 30 · One waySouthwest AirlinesNonstop$135.00
Oct 30 – Nov 2 · 3 nightsSouthwest AirlinesNonstop$260.00
Oct 31 – Nov 7 · 7 nightsSouthwest AirlinesNonstop$260.00

November 2026

Travel datesAirlineStopsTotal price
Nov 13 – Nov 16 · 3 nightsSouthwest AirlinesNonstop$260.00
Nov 14 – Nov 21 · 7 nightsSouthwest AirlinesNonstop$260.00
Nov 24 – Nov 29 · 5 nightsSouthwest AirlinesNonstop$351.00
Nov 27 – Nov 30 · 3 nightsSouthwest AirlinesNonstop$351.00
Nov 28 – Dec 5 · 7 nightsSouthwest AirlinesNonstop$305.50

December 2026

Travel datesAirlineStopsTotal price
Dec 11 – Dec 14 · 3 nightsSouthwest AirlinesNonstop$260.00
Dec 12 – Dec 19 · 7 nightsSouthwest AirlinesNonstop$299.00
Dec 22 – Dec 27 · 5 nightsSouthwest AirlinesNonstop$338.00
Dec 25 – Dec 28 · 3 nightsSouthwest AirlinesNonstop$331.50
Dec 26 – Jan 2 · 7 nightsSouthwest AirlinesNonstop$322.40
Dec 30 – Jan 2 · 3 nightsSouthwest AirlinesNonstop$315.90

January 2027

Travel datesAirlineStopsTotal price
Jan 8 – Jan 11 · 3 nightsSouthwest AirlinesNonstop$247.00
Jan 9 – Jan 16 · 7 nightsSouthwest AirlinesNonstop$247.00
Jan 15 – Jan 18 · 3 nightsSouthwest AirlinesNonstop$247.00
Jan 22 – Jan 25 · 3 nightsSouthwest AirlinesNonstop$247.00
Jan 23 – Jan 30 · 7 nightsSouthwest AirlinesNonstop$247.00

February 2027

Travel datesAirlineStopsTotal price
Feb 5 – Feb 8 · 3 nightsSouthwest AirlinesNonstop$247.00
Feb 6 – Feb 13 · 7 nightsSouthwest AirlinesNonstop$247.00
Feb 12 – Feb 15 · 3 nightsSouthwest AirlinesNonstop$247.00

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$280.00

April 2027

Travel datesAirlineStopsTotal price
Apr 2 – Apr 5 · 3 nightsSouthwest AirlinesNonstop$300.00
Apr 3 – Apr 10 · 7 nightsSouthwest AirlinesNonstop$300.00
Apr 30 – May 3 · 3 nightsSouthwest AirlinesNonstop$300.00

May 2027

Travel datesAirlineStopsTotal price
May 1 – May 8 · 7 nightsSouthwest AirlinesNonstop$300.00
May 28 – May 31 · 3 nightsSouthwest AirlinesNonstop$345.00
May 29 – Jun 5 · 7 nightsSouthwest AirlinesNonstop$322.50

June 2027

Travel datesAirlineStopsTotal price
Jun 25 – Jun 28 · 3 nightsSouthwest AirlinesNonstop$300.00
Jun 26 – Jul 3 · 7 nightsSouthwest AirlinesNonstop$330.00

July 2027

Travel datesAirlineStopsTotal price
Jul 2 – Jul 6 · 4 nightsSouthwest AirlinesNonstop$330.00
Jul 23 – Jul 26 · 3 nightsSouthwest AirlinesNonstop$300.00
Jul 24 – Jul 31 · 7 nightsSouthwest AirlinesNonstop$300.00

August 2027

Travel datesAirlineStopsTotal price
Aug 20 – Aug 23 · 3 nightsSouthwest AirlinesNonstop$300.00
Aug 21 – Aug 28 · 7 nightsSouthwest AirlinesNonstop$300.00

September 2027

Travel datesAirlineStopsTotal price
Sep 3 – Sep 6 · 3 nightsSouthwest AirlinesNonstop$327.00
Sep 17 – Sep 20 · 3 nightsSouthwest AirlinesNonstop$285.00

2026-10-30 · one way · $135.00

  • Southwest Airlines WN900: OMA 2026-10-30 13:35:00 → MDW 2026-10-30 15:00:00; nonstop; 85 minutes. Local airport times.

2026-10-30 → 2026-11-02 · $260.00

  • Southwest Airlines WN900: OMA 2026-10-30 13:35:00 → MDW 2026-10-30 15:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1523: MDW 2026-11-02 10:05:00 → OMA 2026-11-02 11:40:00; nonstop; 95 minutes. Local airport times.

2026-11-14 → 2026-11-21 · $260.00

  • Southwest Airlines WN1222: OMA 2026-11-14 10:35:00 → MDW 2026-11-14 12:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1494: MDW 2026-11-21 21:25:00 → OMA 2026-11-21 23:05:00; nonstop; 100 minutes. Local airport times.

2026-12-11 → 2026-12-14 · $260.00

  • Southwest Airlines WN900: OMA 2026-12-11 13:35:00 → MDW 2026-12-11 15:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1523: MDW 2026-12-14 10:05:00 → OMA 2026-12-14 11:40:00; nonstop; 95 minutes. Local airport times.

2026-12-26 → 2027-01-02 · $322.40

  • Southwest Airlines WN1222: OMA 2026-12-26 10:35:00 → MDW 2026-12-26 12:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1494: MDW 2027-01-02 21:25:00 → OMA 2027-01-02 23:05:00; nonstop; 100 minutes. Local airport times.

2027-01-15 → 2027-01-18 · $247.00

  • Southwest Airlines WN900: OMA 2027-01-15 13:35:00 → MDW 2027-01-15 15:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1523: MDW 2027-01-18 10:05:00 → OMA 2027-01-18 11:40:00; nonstop; 95 minutes. Local airport times.

2027-02-06 → 2027-02-13 · $247.00

  • Southwest Airlines WN1222: OMA 2027-02-06 10:35:00 → MDW 2027-02-06 12:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1494: MDW 2027-02-13 21:25:00 → OMA 2027-02-13 23:05:00; nonstop; 100 minutes. Local airport times.

2027-03-06 → 2027-03-13 · $260.00

  • Southwest Airlines WN1222: OMA 2027-03-06 10:35:00 → MDW 2027-03-06 12:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1494: MDW 2027-03-13 21:25:00 → OMA 2027-03-13 23:05:00; nonstop; 100 minutes. Local airport times.

2027-04-30 → 2027-05-03 · $300.00

  • Southwest Airlines WN900: OMA 2027-04-30 13:35:00 → MDW 2027-04-30 15:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1523: MDW 2027-05-03 10:05:00 → OMA 2027-05-03 11:40:00; nonstop; 95 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $300.00

  • Southwest Airlines WN900: OMA 2027-06-25 13:35:00 → MDW 2027-06-25 15:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1523: MDW 2027-06-28 10:05:00 → OMA 2027-06-28 11:40:00; nonstop; 95 minutes. Local airport times.

2027-07-24 → 2027-07-31 · $300.00

  • Southwest Airlines WN1222: OMA 2027-07-24 10:35:00 → MDW 2027-07-24 12:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1494: MDW 2027-07-31 21:25:00 → OMA 2027-07-31 23:05:00; nonstop; 100 minutes. Local airport times.

2027-09-17 → 2027-09-20 · $285.00

  • Southwest Airlines WN900: OMA 2027-09-17 13:35:00 → MDW 2027-09-17 15:00:00; nonstop; 85 minutes. Local airport times.
  • Southwest Airlines WN1523: MDW 2027-09-20 10:05:00 → OMA 2027-09-20 11:40:00; nonstop; 95 minutes. Local airport times.

More dates for this route