Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

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

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Lowest round trip fares by airline from Pensacola and Chicago

Cheapest prices ($27 One Way, $71 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Jun 26
PNS
Pensacola
ORD
Chicago
$27
Frontier Airlines
Sat, Jul 3
PNS
Pensacola
ORD
Chicago
$44
Frontier Airlines
Sat, Jul 17
PNS
Pensacola
ORD
Chicago
$54
Frontier Airlines
Sat, Jul 10 - Sat, Jul 17
PNS
Pensacola
ORD
Chicago
$71
Frontier Airlines
Sat, Sep 4
PNS
Pensacola
ORD
Chicago
$79
United
Sat, Aug 28
PNS
Pensacola
ORD
Chicago
$79
American Airlines
Sat, Jul 3 - Sat, Jul 10
PNS
Pensacola
ORD
Chicago
$88
Frontier Airlines
Sat, Jun 26 - Sat, Jul 3
PNS
Pensacola
ORD
Chicago
$91
Frontier Airlines
Sat, Jul 10 - Sat, Jul 17
PNS
Pensacola
ORD
Chicago
$128
Frontier Airlines
Tue, Jul 13 - Tue, Jul 20
PNS
Pensacola
ORD
Chicago
$165
American Airlines

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL
The price is $101 per night from Jul 1 to Jul 1
Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...
4.3/5Excellent! (15 reviews)
"I like the bunk beds- so interesting. I love the location. It is close to everything. You are in the heart of the city with lots of activities to do! The staff from day one have been so rude, so cold in attitude just unpleasant but I have tried to beasrespectful and polite as I can possibly be - ..."

Reviewed on Sep 21, 2020

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $116 per night from Jun 27 to Jun 27
Located in The Loop, this hotel is steps from Columbia College Chicago, Grant Park, and State Street. Art Institute of Chicago and Buckingham Fountain are also ...
3/5 (10 reviews)
"I liked the close proximity to downtown, Chicago. The two restaurants on the property as well as close parking in which you would need to pay."

Reviewed on Sep 25, 2020

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $45 per night from Jul 6 to Jul 6
Situated in Elk Grove Village, this motel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Apache Park is 2.9 mi (4.7 km) away.
3.8/5Good! (13 reviews)
"Really nice and clean place. The parking lot was clear."

Reviewed on Feb 23, 2021

Motel 6 Elk Grove Village, IL - O'Hare
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 Pensacola to Chicago

Origin Pensacola
Destination Chicago
Number of Daily Flights 3
Earliest Flight Departure Date Jul 2
Latest Flight Departure Date Jul 2
Popular Airlines United Airlines

Cheap flights from Pensacola to Chicago

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Relax in Chicago 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.