One Way

Popular Filters

+ 1 more

One Way Price

USD 204 USD 400

Duration

2 h 30 m 29 h 0 m

Stops From Chicago

Departure From Chicago

Before 6 AM

USD 208

6 AM - 12 PM

USD 205

12 PM - 6 PM

USD 208

After 6 PM

USD 243

Arrival at Orlando

Before 6 AM

USD 209

6 AM - 12 PM

USD 208

12 PM - 6 PM

USD 205

After 6 PM

USD 208

Alliances & Airlines

Oneworld

(3)

SkyTeam

(2)

Star Alliance

(1)

Layover Airports

+ 1 more

Layover Duration

35 m 23 h 0 m

Top Flights From Chicago

Chicago (CHI) to Orlando (ORL) Cheap Flights

Book Chicago to Orlando cheap flight tickets โœˆ at lowest price. Get best deals on your upcoming Chicago (CHI)to Orlando (ORL) flights only on MakeMyTrip. Also Book Orlando to Chicago Cheap Flights. Currently 18 flights flying from Chicago to Orlando. To save maximum on flight booking click on below Fare Calendar button and choose your dates.

Sorted By:
Departure
Duration
Arrival
Price
Price last updated at 27 Jun 2026 01:06:48
Delta Air Lines

USD 205

Chicago-Midway to Orlando , 30 Jun

Delta Air Lines DL | 4674

09:17

Tue, 30 Jun 26

Chicago-Midway, United States

01 h 18 m

11:35

Tue, 30 Jun 26

Terminal EM

Detroit, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 337

14:00

Tue, 30 Jun 26

Terminal EM

Detroit, United States

02 h 45 m

16:45

Tue, 30 Jun 26

Terminal B

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

USD 208

Chicago-Midway to Orlando , 30 Jun

Southwest Airlines WN | 2815

05:10

Tue, 30 Jun 26

Chicago-Midway, United States

02 h 30 m

08:40

Tue, 30 Jun 26

Terminal A

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines

More Timing Options

USD 209

Chicago to Orlando , 30 Jun

Frontier Airlines F9 | 3241

12:31

Tue, 30 Jun 26

Chicago, United States

02 h 44 m

15:15

Tue, 30 Jun 26

Dallas/Fort Worth, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines F9 | 2886

19:51

Tue, 30 Jun 26

Dallas/Fort Worth, United States

02 h 53 m

23:44

Tue, 30 Jun 26

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

USD 214

Chicago-Midway to Orlando , 30 Jun

Southwest Airlines WN | 496

15:00

Tue, 30 Jun 26

Chicago-Midway, United States

16:40

Tue, 30 Jun 26

Birmingham, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines WN | 496

17:15

Tue, 30 Jun 26

Birmingham, United States

19:55

Tue, 30 Jun 26

Terminal A

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines

USD 231

Chicago to Orlando , 30 Jun

Delta Air Lines DL | 1264

05:30

Tue, 30 Jun 26

Terminal T5

Chicago, United States

02 h 04 m

08:34

Tue, 30 Jun 26

Terminal S

Atlanta, United States

BAGGAGE : CHECK INCABIN

Information not available

Delta Air Lines DL | 1658

09:25

Tue, 30 Jun 26

Terminal S

Atlanta, United States

01 h 32 m

10:57

Tue, 30 Jun 26

Terminal B

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines

USD 232

Chicago to Orlando , 30 Jun

American Airlines AA | 2842

05:10

Tue, 30 Jun 26

Terminal T3

Chicago, United States

02 h 03 m

08:13

Tue, 30 Jun 26

Charlotte, United States

BAGGAGE : CHECK INCABIN

Information not available

American Airlines AA | 2074

10:09

Tue, 30 Jun 26

Charlotte, United States

01 h 49 m

11:58

Tue, 30 Jun 26

Terminal B

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

USD 243

Chicago-Midway to Orlando , 30 Jun

Southwest Airlines WN | 2821

20:10

Tue, 30 Jun 26

Chicago-Midway, United States

02 h 35 m

23:45

Tue, 30 Jun 26

Terminal A

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

United Airlines

USD 249

USD 244

Chicago to Orlando , 30 Jun

United Airlines UA | 284

06:00

Tue, 30 Jun 26

Terminal T1

Chicago, United States

02 h 40 m

09:40

Tue, 30 Jun 26

Terminal B

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

USD 340

Chicago-Midway to Orlando , 30 Jun

Southwest Airlines WN | 2818

12:00

Tue, 30 Jun 26

Chicago-Midway, United States

02 h 40 m

15:40

Tue, 30 Jun 26

Terminal A

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

USD 341

Chicago-Midway to Orlando , 30 Jun

Southwest Airlines WN | 3535

07:55

Tue, 30 Jun 26

Chicago-Midway, United States

02 h 35 m

11:30

Tue, 30 Jun 26

Terminal A

Orlando, United States

BAGGAGE : CHECK INCABIN

Information not available

Chicago to Orlando Flights Information:-

Looking for Chicago to Orlando Flight? Hereโ€™s all you need to know! For convenience and to save time, pick the airport that is closest to your destination. The nearest airport to Orlando is Orlando Airport and the IATA code for the same is ORL.
Currently, there are 5 airlines operating flights between the two destinations and approximately 18 flights take off from Chicago to Orlando every week.

Need information on Chicago to Orlando airfare?

The minimum airfare for a Chicago to Orlando flight would be 204, which may go up to 352 depending on the route, booking time and availability.
It is recommended that you book a round-trip, since it always works out to be more economical.

Flight Details for Chicago to Orlando

If you are looking for Chicago to Orlando flights, there is no dearth of options to choose from. Several reputed airlines currently offer both direct and indirect flights between the two destinations. Some of these are American Airlines, Delta Air Lines, Frontier Airlines, Southwest Airlines, United Airlines. Out of these, only 10 airlines operate direct flights. Indirect flights may involve more travel time, but they usually cost lesser than direct flights.

The number of flights operated by each airline is as follows:American Airlines : 3, Delta Air Lines : 3, Frontier Airlines : 3, Southwest Airlines : 3, United Airlines : 3

To board the first Chicago to Orlando flight, choose Southwest Airlines, which departs at 05:10 The last flight for this route is Southwest Airlines, departing at 20:10

Orlando Airport Information

Orlando Airport
Orlando International Airport
One Jeff Fuqua Blvd
Orlando
Florida
United States
Tel: +1-407-825-2001

About Chicago (CHI)

Chicago, known as the Windy City, is a vibrant metropolis in Illinois, offering an exciting blend of culture, architecture, and entertainment. It boasts iconic landmarks, world-class museums, and a rich history that attracts millions of visitors each year. Whether you're drawn to its towering skyscrapers, picturesque parks, or diverse neighborhoods, Chicago promises a memorable experience for travelers from the United States.

Best Time to Visit

Chicago's weather varies significantly throughout the year. The ideal time to visit is during the spring (April to June) and fall (September to October) when the temperatures are mild, and the city hosts numerous festivals and events. Summer (July to August) is also popular, offering warm weather perfect for outdoor activities and beach visits, though it can be crowded. Winter (December to February) brings cold temperatures and snow, but it transforms the city into a winter wonderland, ideal for those who enjoy winter sports and holiday festivities.

Getting There

Chicago is well-connected to the United States and the world through its two major airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). Both airports offer numerous flights to Chicago, including cheap flights to Chicago from various U.S. cities. United Airlines, American Airlines, and Delta Airlines are among the top carriers providing Chicago flight tickets. Ensure you have a valid ID for domestic flights and a passport for international travel.

Where to Stay

Chicago offers a wide range of accommodations to suit all budgets. For luxury stays, consider the Magnificent Mile area, home to upscale hotels like The Peninsula and Four Seasons. The Loop is ideal for business travelers and those looking to be close to major attractions, with options like the Palmer House Hilton. Budget-conscious travelers can find affordable hotels and hostels in neighborhoods like River North and Lincoln Park.

Must-See Places & Experiences

Chicago is packed with must-see attractions:
โ€ข Millennium Park: Home to the iconic Cloud Gate sculpture (The Bean)
โ€ข Navy Pier: A hub of entertainment with rides, restaurants, and shops
โ€ข Art Institute of Chicago: Renowned for its extensive art collection
โ€ข Willis Tower Skydeck: Offers breathtaking views from the 103rd floor
โ€ข Museum Campus: Includes the Field Museum, Shedd Aquarium, and Adler Planetarium
For a unique experience, explore the city's diverse neighborhoods like Wicker Park and Pilsen, known for their vibrant arts and dining scenes.

Local Transportation

Chicago's public transportation system, operated by the Chicago Transit Authority (CTA), is efficient and affordable. The 'L' trains and buses cover most of the city, making it easy to get around. Taxis and rideshare services like Uber and Lyft are also readily available. For a scenic option, consider taking a water taxi along the Chicago River.

Food & Dining

Chicago is a food lover's paradise, famous for its deep-dish pizza and Chicago-style hot dogs. Must-try dishes include:
โ€ข Deep-dish pizza from Lou Malnati's or Giordano's
โ€ข Chicago-style hot dogs from Portillo's
โ€ข Italian beef sandwiches from Al's Beef
For fine dining, visit Alinea or Girl & The Goat. The city's diverse culinary scene also offers a range of international cuisines, reflecting its multicultural heritage.

Practical Travel Tips

โ€ข Currency: U.S. Dollar (USD)
โ€ข Language: English
โ€ข Safety: Chicago is generally safe for tourists, but it's wise to stay aware of your surroundings and avoid less populated areas at night.
โ€ข Useful Apps: Download the CTA Transit App for public transport info and Yelp for restaurant reviews.
Start planning your trip and explore the best of Chicago with cheap flight tickets to Chicago available on various travel websites. Enjoy your visit to this dynamic city!

Important Information about Chicago to Orlando Flight

Lowest Fare to Travel with Date USD 207- 30 Jun
Total flights from Chicago to Orlando in a week 18 Flights
First Flight Southwest Airlines, departs at 05:10
Last FlightSouthwest Airlines, departs at 20:10
Non-Stop Flights from Chicago to Orlando10
Airport Name & codes of Chicago & Orlando Chicago Midway Intl, Chicago-CHI, Orlando Airport,Orlando-ORL

Chicago Address

About Orlando (ORL)

Rightly called as the โ€˜Theme Park Capital of the World,โ€™ Orlando is a city in the Orange County of the state of Florida. It boasts of a wide collection of theme parks that make it one of the most admired recreational destinations in the world. Adorned with the graceful presence of Lake Eola, this city is best known for the Walt Disney World Resort, which attracts millions of visitors year-round. On a trip to Orlando, travellers can visit the theme parks of Magic Kingdom and Disneyโ€™s Hollywood Studios to take pleasure in a number of fantasy rides, interactive exhibits and fun-filled activities in the Walt Disney World Resort. Downtown Disney is an entertainment and shopping resort that must not be missed by tourists when they are travelling Orlando. Universal Orlando is another resort here, which features a number of theme parks where visitors get to learn and explore, indulge in fun and recreation, and experience a sense of adventure, all at the same time and same place. Besides these, there are also a lot to explore in the downtown area, including a number of historic and cultural attractions. To experience the magic of Disney come alive, there can be no better place than this city. Tourists can grab one of the many exciting and affordable packages from MakeMyTrip to travel around this city conveniently.

Orlando Address

Orlando International Airport
One Jeff Fuqua Blvd
Orlando
Florida
United States
Tel: +1-407-825-2001

Frequently Asked Questions - Chicago to Orlando Flights

Is passport mandatory to travel from Chicago to Orlando?

When making an international trip, passport is mandatory as it defines your identity to the other nation officials. The VISA norms may differ from country to country, which means some would allow Visa on arrival and others may require you to obtain visa in advance. But the availability of passport is mandatory at the time of departure and arrival as well.

Can I cancel my ticket from Chicago to Orlando without cancellation charges?

To avoid cancellation charges on your air tickets, you need to make a selection at the time of booking for ZERO cancellation. Please note, the zero cancellation facility is chargeable with minimum amount and can help you save a lot at the time sudden cancellations.

What is the best time to book cheap flight tickets from Chicago to Orlando?

To get cheap flight tickets from Chicago to Orlando, the best time would be to plan your trip during the off season. At that time the flight tickets are usually cheaper than the peak season and the accommodation booking is also available at the affordable price. The other way of booking cheap flight tickets from Chicago (CHI) to Orlando (ORL) is to book atleast 4 weeks in advance before your departure date to get competitive pricing on your tickets even during the peak season.

How do MakeMyTrip finds the lowest available dare for flights from Chicago to Orlando?

MakeMyTrip is a popular travel portal that also works as a travel search engine that allows you to see best available results for your flight search. Every time you make search for flights to any destination, the MMT algorithm picks all the available air carriers for the route and filter rates basis on the cheapest fare available in their system. At MMT, you can not only search flights on the basis of the fare, but you can also see which flight offers direct route, which has multiple stop-overs, baggage allowance, in-flight meal options, cancellation policy, etc. You can also check available discounts offered by payments partners and air carriers when booking the flight.

Is there a way to make flexible departure date bookings for your Chicago to Orlando flight tickets?

Some travel portals like MakeMyTrip offer flexible departure and arrival booking option with certain air carrier when booking from Chicago to Orlando. You can check the flexible booking flight options once you get the results filters based on your search and make the booking accordingly. Please note, some airlines make charge extra for flexible travel dates.

Can I find cheap accommodation near to airport when travelling from Chicago to Orlando?

There are several accommodation options available near the Orlando Airport. You can check for both budget friendly and well as five star accommodation near the airport depending on your requirement and budget. These hotels are mostly suitable for business travellers.

Which airlines offer cheapest airfare from Chicago to Orlando?

There is no set pricing for airlines to offer cheap flight fare from Chicago to Orlando. These fares are mostly decided on the basis of algorithms followed by air carriers to final the prizing based on demand. However, some multiple route flights with stop-overs offer cheap flights as compared to direct flight departing from Chicago to Orlando.