$105 Find Cheap Flights from Houston Hobby Airport to Chicago Midway Airport - Compare and Save

Among airlines operating Houston Hobby Airport to Chicago Midway Airport flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between Houston Hobby Airport and Chicago Midway Airport.

Flights from Houston Hobby Airport to Chicago Midway Airport usually depart from Houston Hobby (HOU) and arrive at Chicago Midway (MDW).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class
• JetBlue: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Only Economy Class is available on flights from Houston Hobby Airport to Chicago Midway Airport.

On this route, nonstop and layover fares are close on average, with nonstop at $332 round-trip and layover options via Atlanta Hartsfield-Jackson (ATL) at $337.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Airbus A321neo family is used most often on this route, operated mainly by Frontier and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

Most connecting flights from Houston Hobby Airport to Chicago Midway Airport pass through Atlanta Hartsfield-Jackson (ATL), which handles 100% of one-stop traffic on this route. Other layover airports each see under 5%.

On the Houston Hobby Airport to Chicago Midway Airport route, being flexible with your departure day can save you up to 30%. Saturday is the cheapest day at $278 round-trip on average, while Sunday is the most expensive at $397: a $119 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Houston Hobby Airport to Chicago Midway Airport route, 24% of flights were delayed in the past 3 months, with delays averaging 1 hour 54 minutes.

Morning is the busiest departure period on Houston Hobby Airport to Chicago Midway Airport flights, with 50% of flights leaving in that window. Afternoon departures account for 25%, evening flights for 25%, and night flights for 0%.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

These are the earliest and latest flight times available from Houston Hobby Airport to Chicago Midway Airport:

• Earliest: departs at 5:00 am and lands at 7:26 am
• Latest: departs at 10:40 pm and lands at 1:06 am.

The flight takes about 2h 26m.

Last-minute fares on this route - booked within 2 weeks of departure - run 43% above the route average of $331. Book 9 weeks before departure for the lowest fares.

A nonstop flight from Houston Hobby Airport to Chicago Midway Airport takes 2h 26m, covering 938 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $209 to $1,702. That means the highest observed fare was about 8x higher than the lowest one.

One-way fares from Houston Hobby Airport to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $107, which is 50% below the typical average for this route.

Southwest is the only airline operating Houston Hobby Airport to Chicago Midway Airport flights. 76% of its flights are on time.

Morning flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Round-trip flights from Houston Hobby Airport to Chicago Midway Airport range from $246 to $419, with an average of $331 over the past 12 months. Anything below $246 counts as a good deal.

JetBlue is the only airline on the Houston Hobby Airport to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.