Skip to main content
Beginning of main content

Cheap Flights from Chicago to Pensacola $306.13

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Here are your best fares found in the past 7 days

The lowest fare found for this route is $309.32 on Tue, Jun 06 from MDW to PNS
Flights Fare Calendar Find minimum fare between origin MDW and destination PNS Click this button to get previous 30 days data Click this button to get next 30 days data $684 $586 $488 $391 $293 $195 $97 $0 Apr May 26 27 28 29 30 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 1 2 3 4 5 6 7 8 9 10 11 12 13 W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S M T W T F S S Price is $ 586.6 on Delta Price is $ 497.82 on Delta Price is $ 488.6 on Delta Price is $ 487.6 on Delta Price is $ 483.48 on Delta Price is $ 452.41 on Delta Price is $ 445.42 on Delta Price is $ 443.41 on Delta Price is $ 443.4 on Delta Price is $ 442.26 on Delta Price is $ 442.26 on Delta Price is $ 442.26 on Delta Price is $ 436.38 on Delta Price is $ 434.23 on Delta Price is $ 419.22 on Delta Price is $ 411.32 on Delta Price is $ 405.35 on Delta Price is $ 403.62 on Delta Price is $ 403.36 on Delta Price is $ 403.36 on Delta Price is $ 403.36 on Delta Price is $ 402.52 on Delta Price is $ 395.7 on Delta Price is $ 392.1 on Delta Price is $ 390.66 on Delta Price is $ 390.66 on Delta Price is $ 388.66 on Delta Price is $ 388.66 on Delta Price is $ 384.13 on Delta Price is $ 382.72 on Delta Price is $ 382.72 on Delta Price is $ 381.93 on Delta Price is $ 381.7 on Delta Price is $ 380.96 on Delta Price is $ 380.86 on Delta Price is $ 379.66 on Delta Price is $ 378.6 on Delta Price is $ 376.75 on Delta Price is $ 370.34 on Delta Price is $ 369.3 on Delta Price is $ 368.27 on Delta Price is $ 367.92 on Delta Price is $ 366.51 on Delta Price is $ 366.51 on Delta Price is $ 366.51 on Delta Price is $ 366.25 on Delta Price is $ 363.25 on Delta Price is $ 360.29 on Delta Price is $ 359.6 on Delta Price is $ 355.0 on Delta Price is $ 354.98 on Delta Price is $ 352.6 on Delta Price is $ 350.23 on Delta Price is $ 350.23 on Delta Price is $ 342.64 on Delta Price is $ 340.68 on Delta Price is $ 340.68 on Delta Price is $ 340.68 on Delta Price is $ 340.68 on Delta Price is $ 338.97 on Delta Price is $ 335.63 on Delta Price is $ 331.6 on Delta Price is $ 323.99 on Delta Price is $ 322.95 on Delta Price is $ 322.95 on Delta Price is $ 319.81 on Delta Price is $ 319.81 on Delta Price is $ 318.7 on Delta Price is $ 309.32 on Delta

Cheapest Flights from Chicago to Pensacola (MDW to PNS)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Pensacola (MDW to PNS)

Question : Do prices fluctuate more for this route than others?
Answer : Flight prices are fluctuating less for this route than most routes in the United States, as they're ranging from $186 to $866. The further out you book a route, the more likely you are to save.

Question : Which airline can you expect delays with on this route?
Answer : Southwest Airlines is delayed on 12% of flights from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS) at the moment. If you’re on Southwest Airlines, be sure to sign up for the delay notifications to stay up to date with your flight’s status.

Question : How often is the Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS) route delayed?
Answer : This particular route gets passengers to Pensacola International Airport on time 88% of the time, which puts it in the top 50% of the world. When a flight is late, it's a seven-minute delay on average.

Question : Interested in traveling in the next 30 days and want to get the lowest fare?
Answer : As of Apr 24th, the cheapest day to fly from Chicago to Pensacola is May 23rd. Tickets are currently being sold for $317, which is 30% below the average price for this route.

Question : Which airline is giving the best deals for round-trip flights from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS)?
Answer : Delta Air Lines is offering the best deal at $186. Better snatch it up quickly because prices range all the way up to $866 over the next three months.

Question : Is this route your best bet for getting to Pensacola with minimal delays?
Answer : MDW to PNS currently scores 3 out of a possible 5 stars in promptness. This score combines both the number of delayed flights and total delay minutes. With 3 stars, you should feel slightly worried about getting to Pensacola on time.

Question : Will you do what it takes to get the absolute lowest-cost flight?
Answer : The best day to fly on a budget this month is Tuesday. Being flexible with your travel days garners even more savings during booking.