One Way

Popular Filters

+ 1 more

One Way Price

CAD 173 CAD 1,000

Duration

2 h 55 m 29 h 30 m

Stops From Orlando

Departure From Orlando

Before 6 AM

CAD 225

6 AM - 12 PM

CAD 186

12 PM - 6 PM

CAD 173

After 6 PM

CAD 186

Arrival at Chicago

Before 6 AM

CAD 186

6 AM - 12 PM

CAD 218

12 PM - 6 PM

CAD 186

After 6 PM

CAD 173

Airlines

Layover Airports

+ 1 more

Layover Duration

1 h 51 m 22 h 0 m

Top Flights From Chicago

Orlando To Chicago Flights

Book Orlando to Chicago flight tickets at lowest price. Get best deals on your upcoming Orlando to Chicago flights only on MakeMyTrip. Also Book Chicago to Orlando Flights. Currently 19 flights flying from Orlando to Chicago. To save maximum on flight booking click on below Fare Calendar button and choose your dates.Avail Zero Cancellation for flight bookings.


Sorted By:
Departure
Duration
Arrival
Price
Frontier Airlines

CAD 173

Orlando to Chicago-Midway , 3 Apr

Frontier Airlines F9 | 3975

15:24

Fri, 3 Apr 26

Orlando, United States

01 h 47 m

17:11

Fri, 3 Apr 26

Terminal N

Atlanta, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines F9 | 2779

21:15

Fri, 3 Apr 26

Terminal N

Atlanta, United States

02 h 04 m

22:19

Fri, 3 Apr 26

Chicago-Midway, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines

More Timing Options

CAD 186

Orlando to Chicago , 3 Apr

Frontier Airlines F9 | 1554

06:00

Fri, 3 Apr 26

Orlando, United States

01 h 56 m

07:56

Fri, 3 Apr 26

Terminal T2

Durham, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines F9 | 3351

15:57

Fri, 3 Apr 26

Terminal T2

Durham, United States

02 h 29 m

17:26

Fri, 3 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines

CAD 206

Orlando to Chicago , 3 Apr

Frontier Airlines F9 | 3856

09:04

Fri, 3 Apr 26

Orlando, United States

02 h 36 m

11:40

Fri, 3 Apr 26

Terminal E

Philadelphia, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines F9 | 2111

16:41

Fri, 3 Apr 26

Terminal E

Philadelphia, United States

02 h 34 m

18:15

Fri, 3 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines

CAD 212

Orlando to Chicago-Midway , 3 Apr

Frontier Airlines F9 | 3975

15:24

Fri, 3 Apr 26

Orlando, United States

01 h 47 m

17:11

Fri, 3 Apr 26

Terminal N

Atlanta, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines F9 | 2291

19:02

Fri, 3 Apr 26

Terminal N

Atlanta, United States

02 h 05 m

20:07

Fri, 3 Apr 26

Chicago-Midway, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines

CAD 218

Orlando to Chicago , 3 Apr

Frontier Airlines F9 | 3043

06:00

Fri, 3 Apr 26

Orlando, United States

03 h 17 m

08:17

Fri, 3 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines

CAD 225

Orlando to Chicago , 3 Apr

Frontier Airlines F9 | 1563

05:15

Fri, 3 Apr 26

Orlando, United States

01 h 47 m

07:02

Fri, 3 Apr 26

Atlanta, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines F9 | 1441

09:29

Fri, 3 Apr 26

Atlanta, United States

02 h 21 m

10:50

Fri, 3 Apr 26

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines

CAD 232

Orlando to Chicago , 3 Apr

Frontier Airlines F9 | 3274

08:30

Fri, 3 Apr 26

Orlando, United States

02 h 28 m

10:58

Fri, 3 Apr 26

Baltimore, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines F9 | 4307

15:42

Fri, 3 Apr 26

Baltimore, United States

02 h 23 m

17:05

Fri, 3 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Frontier Airlines

CAD 264

Orlando to Chicago , 3 Apr

Frontier Airlines F9 | 2791

21:30

Fri, 3 Apr 26

Orlando, United States

03 h 06 m

23:36

Fri, 3 Apr 26

Terminal T5

Chicago, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

More Timing Options

CAD 640

Orlando to Chicago-Midway , 3 Apr

Southwest Airlines WN | 2300

07:15

Fri, 3 Apr 26

Terminal A

Orlando, United States

03 h

09:15

Fri, 3 Apr 26

Chicago-Midway, United States

BAGGAGE : CHECK INCABIN

Information not available

Southwest Airlines

CAD 969

Orlando to Chicago-Midway , 3 Apr

Southwest Airlines WN | 1739

12:50

Fri, 3 Apr 26

Terminal A

Orlando, United States

02 h 55 m

14:45

Fri, 3 Apr 26

Chicago-Midway, United States

BAGGAGE : CHECK INCABIN

Information not available

Chicago Address

Orlando Address

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

Orlando to Chicago Flights Information:-

Looking for Orlando to Chicago Flight? Here’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 Chicago is Chicago Midway Intl and the IATA code for the same is CHI.
Currently, there are 2 airlines operating flights between the two destinations and approximately 19 flights take off from Orlando to Chicago every week.

Need information on Orlando to Chicago airfare?

The minimum airfare for a Orlando to Chicago flight would be 173, which may go up to 969 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 Orlando to Chicago

If you are looking for Orlando to Chicago 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 Frontier Airlines, Southwest Airlines. Out of these, only 11 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:Frontier Airlines : 11, Southwest Airlines : 11

To board the first Orlando to Chicago flight, choose Frontier Airlines, which departs at 05:15 The last flight for this route is Southwest Airlines, departing at 22:50

Chicago Airport Information

Chicago Midway Intl

About Orlando (ORL)

Rightly called as the ‘Theme Park Capital of the World,’ 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 Disney’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.

About Chicago (CHI)

Chicago is a dazzling city that captivates visitors with its vibrant atmosphere and stunning architecture. For travelers from Canada, Chicago offers an array of experiences, from world-class museums to picturesque waterfront parks. The city's rich cultural heritage and dynamic arts scene make it a must-visit destination.

Best Time to Visit

The ideal time to visit Chicago is during the spring (April to June) and fall (September to November) when the weather is pleasant, and the city is alive with festivals. Summers can be warm and bustling, while winters are cold and snowy, perfect for those who enjoy winter sports.

Getting There

Chicago is served by two major airports: O'Hare International Airport (ORD) and Midway International Airport (MDW). There are numerous flights to Chicago from Canada, including direct flights from Toronto, Vancouver, and Montreal. Ensure you have a valid passport and check visa requirements before booking your flight. Airlines such as Air Canada and United Airlines offer cheap flights to Chicago, making it accessible for Canadian travelers.

Where to Stay

Chicago boasts a wide range of accommodation options to suit all budgets. For luxury, consider staying in the Magnificent Mile area, home to upscale hotels and designer boutiques. Budget travelers can find affordable options in neighborhoods like Lincoln Park and Wicker Park. The Loop, Chicago's downtown area, is ideal for tourists wanting to be close to major attractions.

Must-See Places & Experiences

Chicago is renowned for its iconic landmarks and cultural institutions. Don't miss:
• The Art Institute of Chicago
• Millennium Park and the famous Cloud Gate sculpture
• Navy Pier, offering entertainment and stunning lake views
• Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium
• The Magnificent Mile for shopping
• Willis Tower Skydeck for breathtaking city views

Local Transportation

Chicago's public transportation system is efficient and easy to navigate. The Chicago Transit Authority (CTA) operates buses and trains that connect the city and suburbs. Taxis and ride-sharing services like Uber and Lyft are readily available. For a scenic option, consider renting a bike and exploring the city's extensive bike paths.

Food & Dining

Chicago's culinary scene is diverse and delicious. Be sure to try local specialties such as deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches. The city offers a variety of dining options, from Michelin-starred restaurants to casual eateries. Recommended spots include:
• Lou Malnati's Pizzeria for deep-dish pizza
• Portillo's for Chicago-style hot dogs
• Alinea for an upscale dining experience

Practical Travel Tips

• Currency: The US Dollar (USD)
• Language: English
• Safety: Chicago is generally safe, but be aware of your surroundings and avoid less populated areas at night
• Useful Apps: Download the CTA Transit app for public transport information and OpenTable for restaurant reservations

Start planning your trip and book your Chicago flight today. With so much to offer, Chicago is a city that promises unforgettable experiences for Canadian travelers.

Frequently Asked Questions - Orlando to Chicago Flights

Which airlines offer cheapest airfare from Orlando to Chicago?

There is no set pricing for airlines to offer cheap flight fare from Orlando to Chicago. 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 Orlando to Chicago.

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

There are several accommodation options available near the Chicago Midway Intl. 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.

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

Some travel portals like MakeMyTrip offer flexible departure and arrival booking option with certain air carrier when booking from Orlando to Chicago. 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.

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

To get cheap flight tickets from Orlando to Chicago, 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 Orlando (ORL) to Chicago (CHI) is to book atleast 4 weeks in advance before your departure date to get competitive pricing on your tickets even during the peak season.

Can I cancel my ticket from Orlando to Chicago 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.

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

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 passport mandatory to travel from Orlando to Chicago?

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.