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Flights from Chicago to Pensacola, United States
Chicago to Pensacola Last modified: Mar 26, 2024 19:37 -04:00
We've scanned 117,220,093 round trip itineraries and found the cheapest flights to Pensacola. Spirit & American frequently offer the best deals to Pensacola flights, or select your preferred carrier below to see the cheapest days to fly.
Where To Buy Cheap Flights from Chicago to Pensacola?
The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Chicago to Pensacola based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.
How far in advance should I book tickets from Chicago to Pensacola?
The chart below shows up-to-date information regarding how far in advance to book your flight from Chicago to Pensacola.
| Advanced Purchase | Non Stop | Connecting |
|---|---|---|
| < 7 days | $329 | $253 |
| 7-14 days | $269 | $215 |
| 14-21 days | $269 | $205 |
| 21-30 days | $259 | $205 |
| 30-60 days | $259 | $205 |
| 60-90 days | $259 | $205 |
| 90+ days | $259 | $205 |
Cheap Last Minute Flights from Chicago to Pensacola
Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Pensacola. The chart below shows the best last minute deals and cheap flights this weekend we could find.
Next 30 Days
| Sun | Mon | Tue | Wed | Thu | Fri | Sat |
| 7 | 8 | 9 | 10 | 11 | 12 | 13 |
| $275 | ||||||
| 14 | 15 | 16 | 17 | 18 | 19 | 20 |
| $275 | $225 | |||||
| 21 | 22 | 23 | 24 | 25 | 26 | 27 |
| $225 | $205 | |||||
| 28 | 29 | 30 | 31 | 1 | 2 | 3 |
| $205 | $205 | |||||
| 4 | 5 | 6 | 7 | 8 | 9 | 10 |
| $205 | $208 | |||||
| 11 | 12 | 13 | 14 | 15 | 16 | 17 |
| $208 | ||||||
Connecting Flights vs Direct Flights from Chicago to Pensacola
Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.
The average price for connecting flights from Chicago to Pensacola is not available.
The average price for direct flights from Chicago to Pensacola is not available.
The chart below shows up to date information regarding non-stop flights from Chicago to Pensacola.
| Carrier | Mon | Tue | Wed | Thu | Fri | Sat | Sun | Earliest Flight | Latest Flight |
| United | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 06:35 | 06:35 |
One Way Flights vs Round Trip Flights from Chicago to Pensacola
We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Pensacola. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison. Find Flights
Chicago to Pensacola Flight Questions
Below are some common questions that asked about this flight route:
Farecompare Research Tools
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