Journey information
Overview: Chicago, IL to Pensacola, FL flight
Distance 789 miles (1271 km) |
Average flight duration 2h 24m |
Cheapest ticket price $185 (€150) |
Flights per day 12 |
Fastest flight 4h 27m |
Cheapest month to travel June |
First flight 00:15 |
Last flight 22:10 |
Key Takeaways
Train Ticket Prices
- Budget Options: Train tickets from Chicago, IL to Pensacola, FL start from as low as $185 (€150) if booked well in advance.
- Standard Fares: Typically, trains cost $210 (€171) depending on the train type and class.
The cheapest and fastest flights from Chicago, IL to Pensacola, FL
Cheapest price
$226
Average price
$226
Fastest journey
4 h 27 m
Average duration
4 h 27 m
Flights per day
1
Distance
1271 km
The best way to find a cheap flight ticket from Chicago, IL to Pensacola, FL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Pensacola, FL will cost around $226 if you buy it on the day, but the cheapest tickets can be found for only $226.
Of the 1 flights that leave Chicago, IL for Pensacola, FL onSat, Nov 08, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sat, Nov 08 the direct flights cover the 1271 km distance in an average of 4 h 27 m but if you time it right, some flights will get you there in just 4 h 27 m .
On Sat, Nov 08 the longest flights will take 4 h 27 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.


Compare prices and tickets Chicago, IL to Pensacola, FL by flight
Compare flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Airlines: Allegiant Air from Chicago, IL to Pensacola, FLFind the best flights between Chicago, IL to Pensacola, FL with Omio's travel partners Allegiant Air from $185 (€150). We can find you the best deals, schedules and tickets when comparing and booking the best trip.
Allegiant Air
FAQs: Chicago, IL to Pensacola, FL Flight
Find answers to the most common questions about traveling from Chicago, IL to Pensacola, FL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Pensacola, FL, this guide helps you travel smarter and with confidence.

- Pensacola Seafood Festival, a vibrant celebration of seafood with local vendors, live music, and family-friendly activities
- Blue Angels Homecoming Show, an exhilarating air show featuring the U. S. Navy's elite flight demonstration squadron
- Pensacola Winterfest, a magical holiday event with festive lights, ice skating, and visits from Santa Claus.
- Memorial Day, the unofficial start of summer with vibrant beach activities and local events
- Independence Day, spectacular fireworks and festive celebrations along the coast
- Labor Day, a relaxed atmosphere with warm weather perfect for beach outings.
Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you.
Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
popular airports
Popular airports from Chicago, IL to Pensacola, FL
- Free Wi-Fi available throughout the airport.
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
- Available outside the terminal.
- Elevators, ramps, toilets
- Available throughout the airport.
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
- Lounges available, including United Club and American Airlines Admirals Club.
- Lost and Found located in terminal 1, near the baggage claim area.
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis.
- CTA Blue Line, O'Hare Station, 45 minutes to city center
More options for your journey from Chicago, IL to Pensacola, FL
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