Southwest® flights from Manchester, NH to Chicago-Midway from $149

Promo Code

Low fares from Manchester, NH to Chicago-Midway

$

Manchester, NH (MHT)to

Chicago-Midway (MDW)
Depart: 12/01/2026

One-way

Basic

From
$149
Seen: 13 hrs ago

Manchester, NH (MHT)to

Chicago-Midway (MDW)
Depart: 11/09/2026

One-way

Basic

From
$149
Seen: 22 hrs ago

Manchester, NH (MHT)to

Chicago-Midway (MDW)
Depart: 10/22/2026

One-way

Basic

From
$149
Seen: 20 hrs ago

Manchester, NH (MHT)to

Chicago-Midway (MDW)
Depart: 10/21/2026

One-way

Basic

From
$149
Seen: 10 hrs ago

Manchester, NH (MHT)to

Chicago-Midway (MDW)
Depart: 11/02/2026

One-way

Basic

From
$149
Seen: 15 hrs ago

Manchester, NH (MHT)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$149
Seen: 18 hrs ago

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Explore flights from Manchester, NH to Chicago-Midway

Oct 2026
From$149*
Seen: 20 hrs ago
One Way/Basic
Nov 2026
From$149*
Seen: 18 hrs ago
One Way/Basic
Dec 2026
From$149*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $357
Displaying fares for October-2026
  • MHT–MDW, 10/01/2026: From $333
    01

    Thu

    OCT

  • MHT–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Fri

  • MHT–MDW: cmp-view-offers-disclaimer. Find Offers
    03

    Sat

  • MHT–MDW, 10/04/2026: From $333
    04

    Sun

  • MHT–MDW, 10/05/2026: From $333
    05

    Mon

  • MHT–MDW, 10/06/2026: From $249
    06

    Tue

  • MHT–MDW, 10/07/2026: From $249
    07

    Wed

  • MHT–MDW: cmp-view-offers-disclaimer. Find Offers
    08

    Thu

  • MHT–MDW, 10/09/2026: From $357
    09

    Fri

  • MHT–MDW, 10/10/2026: From $249
    10

    Sat

  • MHT–MDW, 10/11/2026: From $333
    11

    Sun

  • MHT–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Mon

  • MHT–MDW, 10/13/2026: From $333
    13

    Tue

  • MHT–MDW, 10/14/2026: From $259
    14

    Wed

  • MHT–MDW, 10/15/2026: From $309
    15

    Thu

  • MHT–MDW, 10/16/2026: From $309
    16

    Fri

  • MHT–MDW, 10/17/2026: From $274
    17

    Sat

  • MHT–MDW, 10/18/2026: From $335
    18

    Sun

  • MHT–MDW: cmp-view-offers-disclaimer. Find Offers
    19

    Mon

  • MHT–MDW, 10/20/2026: From $249
    20

    Tue

  • MHT–MDW, 10/21/2026: From $149
    21

    Wed

  • MHT–MDW, 10/22/2026: From $149
    22

    Thu

  • MHT–MDW, 10/23/2026: From $165
    23

    Fri

  • MHT–MDW: cmp-view-offers-disclaimer. Find Offers
    24

    Sat

  • MHT–MDW: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • MHT–MDW, 10/26/2026: From $165
    26

    Mon

  • MHT–MDW: cmp-view-offers-disclaimer. Find Offers
    27

    Tue

  • MHT–MDW, 10/28/2026: From $149
    28

    Wed

  • MHT–MDW: cmp-view-offers-disclaimer. Find Offers
    29

    Thu

  • MHT–MDW, 10/30/2026: From $165
    30

    Fri

  • MHT–MDW, 10/31/2026: From $149
    31

    Sat

    • Range$149-$357

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Manchester-Boston Regional Airport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 33 minutes
    Distance:
    838 miles

    Route Information

    113† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 2‡ Nonstop flights on Sunday

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    The average flight time from Manchester, NH to Chicago (Midway) is 2 hours 33 minutes.
    There are 113 weekly flights from Manchester, NH to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Manchester, NH to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Manchester, NH to Chicago (Midway) once per day on Saturdays and 2 times per day on Sundays.
    To find the lowest fares by day and time to fly Manchester, NH to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Manchester, NH to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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