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Lowest round trip fares by airline from Chicago and Pensacola

Cheapest prices ($77 One Way, $188 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Pensacola

Surf & Sand Hotel
2.0 out of 5.0
3.7 out of 5 (7 reviews)

Offering direct access to the beach, this Pensacola Beach hotel is in the city center, 0.1 mi (0.2 km) from Pensacola Beach Pier, and within 9 mi (15 km) of ...

I get saving water and using sheets over but please sweep and mop a floor please. Just a place to sleep.
  
Best Western Beachside Resort
2.5 out of 5.0
3.8 out of 5 (5 reviews)

Nestled on the beach, this Pensacola Beach hotel is within a 15-minute walk of Portofino Boardwalk and Pensacola Beach Pier. Opal Beach and Park West On-Leash ...

The location was nice. Nice having a liquor store in the parking lot for if you needed something. Liked the colors of the rooms
  
Emerald Coast Inn And Suites
2.5 out of 5.0
4.4 out of 5 (8 reviews)

Situated near the beach, this hotel is within a 5-minute walk of Emerald Coast Convention Center and Gulfarium Marine Adventure Park. Wayside Park and Okaloosa ...

Decent enough. Just a place to lay your head. Nothing fancy. Breakfast was ok.
  

Fly From Chicago to Pensacola

OriginChicago
DestinationPensacola
Number of Daily Flights
Earliest Flight Departure Date
Latest Flight Departure Date
Popular Airlines

Cheap flights from Chicago to Pensacola

Chicago to Pensacola

Cheap flights from Chicago to Pensacola

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.