Cheap flights from Chicago (CHI) to Pensacola (PNS)

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Lowest round trip fares by airline from Chicago and Pensacola

Cheapest prices ($225 One Way, $326 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

Surf & Sand Hotel

2 out of 5
40 Fort Pickens Road, Pensacola Beach, FL, 32561
The price is $219 per night from Jul 5 to Jul 6
Stay at this beach hotel in Pensacola Beach. Enjoy free breakfast, free WiFi, and free bicycles on site. Our guests praise the helpful staff and the comfy rooms ...
2.9/5 (9 reviews)
"Staff was friendly.. the first room we were in smelled like smoke and was very loud because of the restaurant/ bar that had a live band.. we didn’t sleep that great that night. But breakfast was always good with friendly staff."

Reviewed on Jun 7, 2022

Surf & Sand Hotel
Emerald Coast Inn And Suites

Emerald Coast Inn And Suites

2.5 out of 5
1214 Miracle Strip Pkwy Se, Fort Walton Beach, FL, 32548
Stay at this business-friendly hotel in Fort Walton Beach. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
4.3/5 Excellent! (6 reviews)
"I was skeptical due to previous bad reviews I saw but I was not disappointed! Our room was clean and smelled fresh!!! The staff were very nice and helpful they came around to ask if we needed towels or anything and our room was cleaned again during our stay upon request. My son enjoyed that their ..."

Reviewed on Sep 19, 2020

Emerald Coast Inn And Suites
At Home Inn & Suites

At Home Inn & Suites

2.5 out of 5
6550 Pensacola Boulevard, Pensacola, FL, 32505
The price is $99 per night from Jul 4 to Jul 5
Stay at this business-friendly hotel in Pensacola. Enjoy free WiFi, a 24-hour front desk, and a 24-hour business center. Our guests praise the pool and the helpful ...
4.3/5 Excellent! (7 reviews)
"Price was fair, floor was really dirty, wore white socks and they were dirty after walking on floor, had to ask them to vacuum. Had noisy neighbors couple of times, could hear through adjoining doors. Would I stay there again only if it was the only thing available."

Reviewed on Feb 24, 2022

At Home Inn & Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Chicago to Pensacola

Origin Chicago
Destination Pensacola
Number of Daily Flights 3
Earliest Flight Departure Date Jul 9
Latest Flight Departure Date Jul 9
Popular Airlines

Cheap flights from Chicago to Pensacola

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Save Even More Time and Money With a Pensacola Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Pensacola vacation that you can't get when you book flights and hotel separately.

Relax in Pensacola With Confidence and Convenience

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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.