Winter Park, FL to Chicago, IL Flights

Cheap plane tickets from Winter Park, FL to Chicago, IL can start from as little as $207 (€168) when you book in advance. The average flight ticket price for Winter Park, FL to Chicago, IL is $207 (€168); however, prices vary depending on the time of day and class and they tend to be more expensive on the day.

The average journey time by plane from Winter Park, FL to Chicago, IL is 8 h 14 min   to travel the 979 mile (1579 km) long trip, with around there are 58 flights per day. Journey times can vary on weekends and holidays.

The earliest flight from Winter Park, FL to Chicago, IL leaves at 5: 00AM. Plan your trip with the Journey Planner   from Omio.

The latest flight from Winter Park, FL to Chicago, IL leaves at 11: 55PM.

The cheapest month for a flight from Winter Park, FL to Chicago, IL is April.

You have options as you can travel from Winter Park, FL to Chicago, IL 2 different ways: train or flight.

Since neither Winter Park, FL nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of USA and USA. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.

There is a time difference of 1 h between Winter Park, FL and Chicago, IL all year round.

The best events to attend in Chicago, IL include:

• Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan
• Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park
• Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.

The best holidays to experience in Chicago, IL include:

• Memorial Day, the unofficial start of summer with vibrant outdoor activities and events
• Independence Day, spectacular fireworks and festive celebrations throughout the city
• Labor Day, a lively atmosphere with various festivals and pleasant weather.

The best seasons to visit Chicago, IL are Spring or Summer. The best weather to explore Chicago, IL is during May-September.

For domestic flights we recommend to arrive 1.5 to 2 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.

Most airlines permit carry-on bags that fit within specific dimensions (e. G. 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.

Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs).
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.

The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.