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Flight Deals from Chicago to Orlando from $84

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Price Drop Deals Near You

Orlando

56% Price Drop

May 17

ORD

3 days

May 20

MCO

$250

now only

$109

Round-trip

Orlando

54% Price Drop

May 20

ORD

3 days

May 23

MCO

$250

now only

$114

Round-trip

Orlando

51% Price Drop

May 16

ORD

4 days

May 20

MCO

$250

now only

$123

Round-trip

Orlando

46% Price Drop

May 14

ORD

4 days

May 18

MCO

$250

now only

$134

Round-trip

Orlando

43% Price Drop

May 15

ORD

5 days

May 20

MCO

$250

now only

$143

Round-trip

Orlando

26% Price Drop

May 23

ORD

3 days

May 26

MCO

$250

now only

$184

Round-trip

Orlando

26% Price Drop

May 27

ORD

5 days

Jun 1

MCO

$249

now only

$185

Round-trip

Orlando

26% Price Drop

May 30

ORD

4 days

Jun 3

MCO

$250

now only

$185

Round-trip

Orlando

24% Price Drop

May 13

ORD

3 days

May 16

MCO

$250

now only

$189

Round-trip

Orlando

22% Price Drop

May 18

ORD

3 days

May 21

MCO

$250

now only

$195

Round-trip

Stops

  • Up to 1 stop
    $113
  • Up to nonstop
    $119

Airlines

  • Alaska Airlines
    $831
  • American Airlines
    $183
  • CitizenPlane
    $127
  • Delta Air Lines
    $196
  • Frontier Airlines
    $113
  • Hahn Air
    $204
  • JetBlue
    $771
  • Southwest Airlines
    $183
  • United Airlines
    $183

Cabin Class

  • Economy
    $113

Departure Airports

  • Chicago Midway Airport
    $113
  • Chicago O Hare Airport
    $113

Arrival Airports

  • Orlando International Airport
    $113

Layover Airports

  • General Edward Lawrence Logan International Airport
    $771
  • Hartsfield Jackson Atlanta International Airport
    $113
  • San Diego International Airport
    $831

Best Price. GUARANTEED.

Exclusively for Priceline Members
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Frontier Airlines Logo
Frontier Airlines

05/19/26

MDW
8h 23m
ATL

05/19/26

MCO
Frontier Airlines Logo
Frontier Airlines

05/23/26

MCO
3h 15m
Direct

05/23/26

ORD
$113
Frontier Airlines Logo
Frontier Airlines

05/15/26

ORD
3h 2m
Direct

05/15/26

MCO
Frontier Airlines Logo
Frontier Airlines

05/20/26

MCO
3h 15m
Direct

05/20/26

ORD
$119
Frontier Airlines Logo
Frontier Airlines

05/15/26

ORD
3h 2m
Direct

05/15/26

MCO
Frontier Airlines Logo
Frontier Airlines

05/20/26

MCO
3h 15m
Direct

05/20/26

ORD
$127
Bundle + Save
Book a flight & hotel together for extra savings.
On average save $240 per traveler
United Airlines Logo
United Airlines

06/02/26

ORD
2h 59m
Direct

06/02/26

MCO
United Airlines Logo
United Airlines

06/04/26

MCO
3h 9m
Direct

06/04/26

ORD
$183
American Airlines Logo
American Airlines

06/02/26

ORD
2h 51m
Direct

06/02/26

MCO
American Airlines Logo
American Airlines

06/04/26

MCO
3h 8m
Direct

06/04/26

ORD
$183
Southwest Airlines Logo
Southwest Airlines

05/18/26

ORD
2h 45m
Direct

05/18/26

MCO
Southwest Airlines Logo
Southwest Airlines

05/19/26

MCO
3h 10m
Direct

05/19/26

ORD
$183
Delta Air Lines Logo
Delta Air Lines

06/16/26

MDW
4h 40m
ATL

06/16/26

MCO
Delta Air Lines Logo
Delta Air Lines

06/24/26

MCO
4h 58m
ATL

06/24/26

ORD
$196
Southwest Airlines Logo
Southwest Airlines

05/18/26

ORD
2h 45m
Direct

05/18/26

MCO
Southwest Airlines Logo
Southwest Airlines

05/19/26

MCO
3h 10m
Direct

05/19/26

ORD
$204
American Airlines Logo
American Airlines

05/18/26

ORD
2h 48m
Direct

05/18/26

MCO
American Airlines Logo
American Airlines

05/20/26

MCO
3h 16m
Direct

05/20/26

ORD
$263
United Airlines Logo
United Airlines

05/15/26

ORD
2h 55m
Direct

05/15/26

MCO
United Airlines Logo
United Airlines

05/20/26

MCO
3h 13m
Direct

05/20/26

ORD
$327
JetBlue Logo
JetBlue

05/13/26

ORD
8h 48m
BOS

05/13/26

MCO
JetBlue Logo
JetBlue

05/20/26

MCO
14h 23m
BOS

05/20/26

ORD
$771
Alaska Airlines Logo
Alaska Airlines

05/17/26

ORD
19h 8m
SAN

05/18/26

MCO
Alaska Airlines Logo
Alaska Airlines

05/18/26

MCO
17h 46m
SAN

05/18/26

ORD
$831

Top Deals on flights from Chicago to Orlando

Chicago, US (CHI) - Orlando, US (ORL)

American Airlines Logo
American Airlines

Jun 2

ORD
2h 51m
Direct

Jun 2

MCO

as low as

$84

Chicago, US (CHI) - Orlando, US (ORL)

Delta Air Lines Logo
Delta Air Lines

Jun 23

MDW
5h 41m
ATL

Jun 23

MCO

as low as

$98

Chicago, US (CHI) - Orlando, US (ORL)

Southwest Airlines Logo
Southwest Airlines

May 16

ORD
2h 45m
Direct

May 16

MCO

as low as

$117

Chicago, US (CHI) - Orlando, US (ORL)

 Logo

May 16

ORD
2h 40m
Direct

May 16

MCO

as low as

$170

Chicago, US (CHI) - Orlando, US (ORL)

Southwest Airlines Logo
Southwest Airlines

May 16

ORD
2h 40m
Direct

May 16

MCO

as low as

$178

Good to Know

Essential information to help you plan your flight from Chicago to Orlando

Cheapest Flight

$84

The lowest price we found in the last two weeks, departing Jun 2 and returning Jun 2

Airline AA2h 51m ‧ economy

Fastest Flights

$170

The fastest flight that we found in the last two weeks, departing May 16 and returning May 16

Airline NK2h 40m ‧ economy

Cheapest Flight Round-trip

$113

Cheapest price found in the last 14 days, departing May 19 and returning May 23

Airline F91 stop ‧ 8h 23m ‧ economy

Cheapest Flight One-way

$84

Cheapest price found in the last 14 days, departing Jun 2

Airline AA2h 51m ‧ economy

Cheapest Layover airport

$98

The cheapest layover airport to Orlando is currently $98

Airline DL1 stop ‧ 5h 41m ‧ economy

Best Arrival airport

$84

The best arrival airport to Orlando is currently $84

Airline AA2h 51m ‧ economy

Best Departure airport

$84

The best departure airport to Orlando is currently $84

Airline AA2h 51m ‧ economy

Cheapest Airline

$84

The cheapest airline to Orlando is currently $84

Airline AA2h 51m ‧ economy

Peak prices from Chicago to Orlando occur in late March to early April, while the lowest fares are found in mid-September.

When planning your flights from Chicago to Orlando, consider that the most expensive times typically fall between late March and early April, where prices peak around $289. Conversely, one of the lowest price periods is mid-September, with fares dropping to around $153. Generally, the high season is concentrated from mid-March to late April and late May through early July, with price variations of about $60 to $100 compared to the low season, which is in early January and September. The seasonal transitions are abrupt, especially from mid-March to late March.

Book from 25 to 36 days before departure to secure the lowest prices for your Chicago to Orlando trip.

For your trip from Chicago to Orlando, the best time to buy tickets is between 25 to 36 days before departure, with the most affordable prices seen around 33 days prior, typically ranging from $197. Booking earlier than this can lead to significantly higher costs, up to $325, which is a 65% increase. Prices remain reasonably low until about 15 days before departure but become volatile and ultimately increase rapidly from $200 to as high as $402 as the departure date approaches. Therefore, it's advisable to purchase your tickets well in advance to avoid higher prices.

Frequently Asked Questions

What is the typical flight duration from Chicago to Orlando?

The flight duration from Chicago to Orlando typically takes between 3 to 4 hours. Direct flights tend to be on the shorter end, while connecting flights might extend the journey closer to 4 hours. Weather conditions and flight paths can add slight variations, so it’s wise to allow some flexibility in your travel plans. This range gives travelers from Chicago a solid idea for scheduling their travels and making timely connections, ensuring a smoother trip overall.

Are there any direct flights available from Chicago to Orlando?

Yes, direct flights are available from Chicago to Orlando. These non-stop services usually offer a flight time of about 3 to 4 hours, making the journey efficient for travelers. Direct options minimize the hassles of layovers and connect more directly with arrival schedules. However, availability and prices may fluctuate depending on the travel season or day. It is beneficial for visitors from Chicago to review multiple flight options and book early to secure the best rates and convenient timings.

What are the best transportation options from Orlando airport to downtown or popular attractions?

Travelers arriving from Chicago can choose from a variety of transportation options at Orlando airport. Rideshare services like Uber and Lyft or traditional taxis typically charge between $25 and $50 for trips to downtown areas or major attractions. Shuttle services offer a more economical choice, usually ranging from $15 to $30 per person, while rental car options provide freedom to explore and cost anywhere from $30 to $70 daily. Comparing these options before arrival ensures a smooth and efficient transition to your destination.

What are the must-see attractions in Orlando for travelers arriving from Chicago?

Orlando boasts a range of must-see attractions ideal for visitors from Chicago. Iconic theme parks such as Walt Disney World, Universal Studios, and SeaWorld offer immersive entertainment and family fun. Additionally, attractions like ICON Park provide scenic rides and diverse dining experiences. For a cultural touch, consider exploring local museums or themed districts that reveal the area’s history and artistic flair. Balancing high-adrenaline thrills with cultural stops can create a well-rounded itinerary for an unforgettable visit.

Which local dishes should travelers from Chicago try when visiting Orlando?

Travelers from Chicago should savor Orlando’s diverse culinary scene by sampling dishes that reflect its multicultural influences. Popular options include Cuban sandwiches, fresh seafood dishes featuring locally sourced fish, and the much-loved Key Lime Pie with its unique regional twist. For those feeling adventurous, some eateries even offer fried gator bites. Exploring local food markets and small neighborhood restaurants can provide authentic tastes and a true insight into the local flavor, making your dining experience both memorable and enriching.

What are the best family-friendly activities in Orlando for visitors from Chicago?

Orlando offers an abundance of family-friendly activities perfect for visitors from Chicago. World-famous theme parks like Walt Disney World, Universal Studios, and SeaWorld provide a range of attractions suitable for all ages. In addition, interactive venues such as the Orlando Science Center and numerous water parks deliver fun and educational experiences. Outdoor activities in local parks and seasonal events further enhance the family experience. Carefully planning a mix of these attractions ensures an engaging and entertaining visit for every member of the family.

What are the most affordable dining options in Orlando for travelers from Chicago?

Orlando features a variety of affordable dining options for visitors traveling from Chicago. Budget-friendly choices include food trucks, casual diners, and local cafes where meals typically range from $10 to $20. Neighborhood eateries serve up authentic Cuban sandwiches, comfort food, and pizza at reasonable prices, while local markets often offer daily specials. Exploring areas outside the main tourist zones can reveal hidden culinary gems that combine distinctive flavors with friendly prices. This approach allows you to enjoy an authentic dining experience without straining your travel budget.

Is there a specific time of year when Orlando is best visited by travelers from Chicago?

Yes, the optimal times to visit Orlando for travelers from Chicago are typically during the spring (March through May) and fall (September through November). These seasons offer pleasant weather, moderate crowd levels, and a balance between entertaining attractions and relaxed sightseeing. While summers can be vibrant, they also tend to be hot and crowded, and winter holidays may bring higher prices. Selecting travel dates during these shoulder seasons ensures a more enjoyable and comfortable experience while taking full advantage of local events and outdoor activities.

What are the customs requirements for travelers flying from Chicago to Orlando?

While international travel often involves customs procedures, these requirements are not applicable for a domestic journey between Chicago and Orlando. Travelers only need to comply with standard TSA security and identification checks at airports. A government-issued photo ID is sufficient for boarding and passing through security. It is always a good practice to verify any specific airline protocols or airport procedures in advance. This ensures a smooth and hassle-free travel experience since customs requirements do not apply to residents flying within the United States.

Are there any seasonal events in Orlando that travelers from Chicago should not miss?

Yes, Orlando hosts several seasonal events that are a must-see for visitors from Chicago. In the spring, the Epcot International Flower and Garden Festival draws crowds with its vibrant landscapes and unique food offerings. Summer brings lively outdoor concerts and water events, while fall introduces themed festivals and Halloween celebrations across major attractions. Winter in Orlando features festive parades and dazzling holiday light displays. Checking local event calendars ahead of time will help you plan your visit to coincide with these memorable cultural and entertainment experiences.

What are the best car rental options in Orlando for travelers from Chicago?

For visitors from Chicago, Orlando offers a range of car rental options from reputable companies such as Enterprise, Hertz, Avis, and Budget. Daily rates typically range from $30 to $70, depending on the type of vehicle and rental duration. It is wise to compare prices and consider advance bookings to secure special discounts or package deals. Additionally, many companies offer flexible rental terms and loyalty programs, which can be beneficial for longer stays or frequent travelers. These options allow you to choose the most convenient vehicle to explore various attractions comfortably.

What unique cultural attractions can travelers from Chicago explore in Orlando?

Travelers from Chicago can immerse themselves in Orlando's distinct cultural attractions that extend beyond its theme parks. Key highlights include the Charles Hosmer Morse Museum of American Art, renowned for its extensive collection of Tiffany glass, and the Orlando Museum of Art, which showcases local and regional talent. For history enthusiasts, Fort Christmas Historical Park offers a glimpse into the area’s past, while local neighborhoods boast live music venues and artisan markets. These unique cultural sites provide enriching experiences that highlight Orlando’s artistic heritage and diverse community.

What safety tips should travelers from Chicago keep in mind while visiting Orlando?

Travelers from Chicago should adopt several safety practices while visiting Orlando. Remain vigilant in crowded public areas, such as theme parks and downtown districts, where pickpocketing can occur. Monitor local weather forecasts, as tropical rain showers may require sudden adjustments to your plans. Always secure your belongings and use reputable transportation options like licensed taxis or rideshare services. Additionally, familiarize yourself with local emergency contacts and stay informed about any travel advisories in the area. These precautions help ensure that your visit remains both enjoyable and secure.

Are there any pet-friendly services available at Orlando airport for travelers from Chicago?

Yes, Orlando airport offers several pet-friendly services for travelers from Chicago. The airport is equipped with designated pet relief areas to ensure your animal's comfort during transit. Many airline carriers and nearby accommodations are also pet-friendly, providing extra support for those traveling with furry companions. It is a good idea to review the specific pet policies of your carrier beforehand, as fees and restrictions may apply. Taking these steps helps guarantee a smooth and stress-free travel experience for both you and your pet during your stay.

What are the best shopping areas in Orlando for travelers from Chicago looking for souvenirs?

Travelers from Chicago looking for unique souvenirs have plenty of shopping areas to explore in Orlando. Disney Springs offers an array of themed boutiques, specialty shops, and local art displays ideal for memorable finds. The Mall at Millennia provides a mix of upscale and mid-range retail options, while downtown Orlando and nearby artisan markets present independent boutiques selling handcrafted items. These locations cater to a variety of tastes and budgets, making it easier to find the perfect keepsake that captures the essence of the local culture and vibrant spirit of the area.

Flights to Orlando