$139 Find Cheap Flights from Hartford to Chicago Midway Airport - Compare and Save

Among airlines operating Hartford 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 Hartford and Chicago Midway Airport.

Flights from Hartford to Chicago Midway Airport usually depart from Hartford Bradley Intl (BDL) 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

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

Two cabin classes are available on flights from Hartford to Chicago Midway Airport:

• Economy Class
• First Class

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $153 round-trip via Orlando (MCO), compared to $413 for nonstop.

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 Boeing 737-800 family is used most often on this route, operated mainly by American Airlines and United Airlines. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

One-stop flights from Hartford to Chicago Midway Airport most commonly connect through:

• Detroit Metropolitan Wayne County (DTW) - 61% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 17% of one-stop connections
• Orlando (MCO) - 17% of one-stop connections
• Baltimore/Washington (BWI) - 4% of one-stop connections

Detroit Metropolitan Wayne County (DTW) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 16% on the Hartford to Chicago Midway Airport route. Tuesday is the cheapest departure day at $371 round-trip on average, while Wednesday is the most expensive at $437, a difference of $66. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Morning is the busiest departure period on Hartford to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, 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 Hartford to Chicago Midway Airport:

• Earliest: departs at 6:50 am and lands at 9:14 am
• Latest: departs at 8:15 pm and lands at 10:39 pm.

The flight takes about 2h 24m.

Last-minute fares on this route - booked within 2 weeks of departure - run 62% above the route average of $408. Book 17 weeks before departure for the lowest fares.

A nonstop flight from Hartford to Chicago Midway Airport takes 2h 24m, covering 773 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 $284 to $2,061. That means the highest observed fare was about 7x higher than the lowest one.

One-way fares from Hartford to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $144, which is 46% below the typical average for this route.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 14m, compared with 5h 19m via Baltimore/Washington (BWI) and 6h 48m via Atlanta Hartsfield-Jackson (ATL).

Chicago Midway Airport is 1 hour behind Hartford (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

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 Hartford to Chicago Midway Airport range from $346 to $482, with an average of $408 over the past 12 months. Anything below $346 counts as a good deal.