Flight Routes from Houston Hobby to Chicago Midway

Compare cheap outbound and return flights from Houston-Hobby (HOU) to Chicago Midway (MDW) and find the best offer from numerous airlines and travel agencies.

Trip type
Cheapest roundtrip flight
from€255
Fastest flight
non-stop flights
108x / week
Flight distance
1,511 km
Time difference
none

Cheap flight offers from Houston Hobby to Chicago Midway

sorted by price and recency
filters
  1. –
    American Airlines
    –
    HOU–MDW
    3 stopovers
    LATAM Chile
    –
    MDW–HOU
    4 stopovers
    €3,033
  2. –
    Southwest Airlines
    –
    HOU–MDW
    non-stop flight
    Southwest Airlines
    –
    MDW–HOU
    non-stop flight
    €255

Flight schedule from Houston-Hobby (HOU) to Chicago Midway (MDW)

Select a travel date in the flight schedule for the route from Houston-Hobby (HOU) to Chicago Midway (MDW) and compare affordable flight deals.

offers
Active filtersnone
Matching outbound flightsHOU–MDW · 22 of 22
fromto
dep.arr.
durationstopovers
  1. November 8 – 14, 2026
  2. November 15 – 21, 2026
  3. November 22 – 28, 2026
    1. HOUMDW
      nonstop
      1. Southwest Airlines
    2. HOUMDW
      nonstop
      1. Southwest Airlines
    3. HOUMDW
      nonstop
      1. Southwest Airlines
    4. HOUMDW
      nonstop
      1. Southwest Airlines
    5. HOUMDW
      nonstop
      1. Southwest Airlines
    6. HOUMDW
      nonstop
      1. Southwest Airlines
    7. HOUMDW
      nonstop
      1. Southwest Airlines
    8. HOUMDW
      nonstop
      1. Southwest Airlines
    9. HOUMDW
      nonstop
      1. Southwest Airlines
    10. HOUMDW
      nonstop
      1. Southwest Airlines
    11. HOUMDW
      nonstop
      1. Southwest Airlines
    12. HOUMDW
      nonstop
      1. Southwest Airlines
    13. HOUMDW
      nonstop
      1. Southwest Airlines
    14. HOUMDW
      nonstop
      1. Southwest Airlines
    15. HOUMDW
      nonstop
      1. Southwest Airlines

      Important flight information

      Discover more flights around Houston-Hobby and Chicago Midway

      Departure airport Airport Houston-Hobby, Airport, TX (HOU)
      Arrival airport Airport Chicago Midway International Airport, IL (MDW)
      Destination country Flights to United States
      City-Code - Arrival airport Houston - Metro - Chicago Midway International Airport, IL
      Departure airport - Destination country Houston-Hobby, Airport, TX - United States
      Departure airport - City-Code Houston-Hobby, Airport, TX - Chicago
      Alternative routes to United States
      Alternative flights to Chicago Midway
      Flight destinations with a similar price
      Flight destinations with a similar price