$142 Find Cheap Flights from Houston Hobby Airport to Chicago - Compare and Save

Travelers can relax and unwind at some of the luxury hotels located within Midway Airport, like Residence Inn Midway Airport hotel located just 1 mile away from the terminal. You can stay at the Hilton O'Hare Airport Hotel right across T1, T2, and T3.

Those with limited mobility can receive baggage and wheelchair assistance from Skycap Service. The airport also has wheelchair-accessible restrooms and elevators. Those with disabilities should communicate any other assistance they may require through the airline before their departure date.

There is a nursing room on Concourse C at Midway Airport. Most restrooms at Midway Airport have baby-changing stations. You will also find kid-friendly restaurants at the airport. There is a kids'play area in Terminal 2 of O'Hare Airport. Nursing rooms are also available at Terminals 1 to 5.

An affordable parking lot at Hobby Airport is the Ecopark, where you can leave your car for a fee of around $9. Another option is the Terminal Parking garage, which charges around $13 for the daily parking option. Valet parking is also available for around $28 per day.

Among airlines operating Houston Hobby Airport to Chicago 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.

Flights from Houston Hobby Airport to Chicago usually depart from Houston Hobby (HOU) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

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.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $332 round-trip, compared to $383 via a layover through Atlanta Hartsfield-Jackson (ATL).

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.

Connecting flights from Houston Hobby Airport to Chicago most commonly pass through:

• Atlanta Hartsfield-Jackson (ATL) - 67% of one-stop connections
• Dallas/Fort Worth (DFW) - 33% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.

On the Houston Hobby Airport to Chicago route, being flexible with your departure day can save you up to 33%. Saturday is the cheapest day at $278 round-trip on average, while Sunday is the most expensive at $412: a $134 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 route, 23% 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 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 are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

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

• 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 $332. Book 9 weeks before departure for the lowest fares.

A nonstop flight from Houston Hobby Airport to Chicago takes 2h 26m, covering 946 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 $283 to $1,678. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Houston Hobby Airport to Chicago are currently lower than usual. Average one-way flight prices are about $148, which is 31% below the typical average for this route.

Southwest is the only airline operating Houston Hobby Airport to Chicago flights. 77% 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.

Flying via Dallas/Fort Worth (DFW) gives the shortest average 1-stop total travel time at 4h 58m, compared with 5h 18m via Atlanta Hartsfield-Jackson (ATL).

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

· Routes Car & Truck Rentals
· Europcar
· Hertz
· Dollar
· Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

· Hertz
· Dollar
· Budget
· Alamo
· Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

· Alamo
· Enterprise Rent-A-Car
· Budget
· Avis
· National

Round-trip flights from Houston Hobby Airport to Chicago range from $246 to $428, with an average of $332 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 route offering in-flight Wi-Fi. Pricing depends on fare class.