$121 Find Cheap Flights from Pensacola to Chicago Midway Airport - Compare and Save

Among airlines operating Pensacola to Chicago Midway Airport flights:

• Southwest: offers free seat selection

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

Flights from Pensacola to Chicago Midway Airport usually depart from Pensacola (PNS) 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 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 Pensacola to Chicago Midway Airport.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $367 round-trip via Nashville Intl (BNA), compared to $398 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 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Embraer 175 variants.

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

• Atlanta Hartsfield-Jackson (ATL) - 56% of one-stop connections
• Nashville Intl (BNA) - 38% of one-stop connections
• Lambert-St Louis (STL) - 6% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 32% on the Pensacola to Chicago Midway Airport route. Wednesday is the cheapest departure day at $298 round-trip on average, while Monday is the most expensive at $436, a difference of $138. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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.

A nonstop flight from Pensacola to Chicago Midway Airport takes 0h 00m, covering 782 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 $314 to $1,966. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Pensacola to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $150, which is 31% below the typical average for this route.

Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 3h 53m, compared with 4h 24m via Nashville Intl (BNA) and 4h 33m via Atlanta Hartsfield-Jackson (ATL).

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 Pensacola to Chicago Midway Airport range from $321 to $466, with an average of $395 over the past 12 months. Anything below $321 counts as a good deal.