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Flight Deals from Orlando to Chicago O Hare Airport from $47

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Stops

  • Nonstop
    from $97
  • Up to 1 stop
    $141
  • Up to 2 stops
    $297

Airlines

  • American Airlines
    $248
  • Delta Air Lines
    $198
  • Frontier Airlines
    $97
  • JetBlue
    $278
  • Spirit Airlines
    $119
  • United Airlines
    $248

Cabin Class

  • Economy
    $97

Departure Airports

  • Orlando International Airport
    $97

Arrival Airports

  • Chicago O Hare Airport
    $97

Layover Airports

  • Charlotte Douglas International Airport
    $287
  • Dallas Fort Worth International Airport
    $330
  • Detroit Metropolitan Airport
    $198
  • Fort Lauderdale Hollywood International Airport
    $155
  • George Bush Intercontinental Houston Airport
    $262
  • Harry Reid International Airport
    $162
  • Hartsfield Jackson Atlanta International Airport
    $141
  • Miami International Airport
    $311
  • Myrtle Beach International Airport
    $167
  • New York John F Kennedy Airport
    $278
  • Philadelphia International Airport
    $287
  • Reagan Washington National Airport
    $297
  • Washington Dulles Airport
    $258

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On average save $240 per traveler
Frontier Airlines Logo
Frontier Airlines

05/23/25

MCO
2h 3m
Direct

05/24/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/24/25

ORD
3h 57m
Direct

05/24/25

MCO
$97
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/22/25

MCO
2h 3m
Direct

05/23/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/25/25

ORD
3h 54m
Direct

05/25/25

MCO
$97
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/25/25

MCO
2h 8m
Direct

05/25/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/28/25

ORD
3h 39m
Direct

05/28/25

MCO
$119
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/23/25

MCO
2h 4m
Direct

05/23/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/25/25

ORD
3h 45m
Direct

05/25/25

MCO
$129
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/19/25

MCO
3h 40m
ATL

05/19/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/21/25

ORD
3h 39m
Direct

05/21/25

MCO
$141
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/16/25

MCO
3h 40m
ATL

05/16/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/19/25

ORD
3h 45m
Direct

05/19/25

MCO
$151
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/25/25

MCO
2h 8m
Direct

05/25/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/28/25

ORD
7h 56m
FLL

05/28/25

MCO
$155
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/18/25

MCO
8h 44m
LAS

05/19/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/25/25

ORD
3h 57m
Direct

05/25/25

MCO
$162
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/23/25

MCO
3h 13m
MYR

05/23/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/25/25

ORD
3h 45m
Direct

05/25/25

MCO
$167
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/09/25

MCO
2h 9m
Direct

05/09/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/18/25

ORD
11h 16m
LAS

05/19/25

MCO
$174
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/20/25

MCO
2h 8m
Direct

05/20/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/21/25

ORD
7h 56m
FLL

05/21/25

MCO
$186
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/25/25

MCO
4h 33m
ATL

05/25/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/25/25

ORD
5h 48m
DTW

05/25/25

MCO
$198
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/24/25

MCO
5h 32m
ATL

05/24/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/25/25

ORD
5h 46m
DTW

05/25/25

MCO
$198
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/23/25

MCO
3h 13m
MYR

05/23/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/26/25

ORD
6h 41m
MYR

05/26/25

MCO
$205
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/25/25

MCO
2h 7m
Direct

05/25/25

ORD
United Airlines Logo
United Airlines

05/25/25

ORD
3h 56m
Direct

05/25/25

MCO
$248
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

MCO
2h 7m
Direct

05/25/25

ORD
American Airlines Logo
American Airlines

05/25/25

ORD
3h 43m
Direct

05/25/25

MCO
$248
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/24/25

MCO
2h 14m
Direct

05/24/25

ORD
United Airlines Logo
United Airlines

05/25/25

ORD
3h 47m
Direct

05/25/25

MCO
$248
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/24/25

MCO
4h 45m
IAD

05/24/25

ORD
United Airlines Logo
United Airlines

05/25/25

ORD
3h 59m
Direct

05/25/25

MCO
$258
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/03/25

MCO
5h 21m
IAH

05/03/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/06/25

ORD
3h 46m
Direct

05/06/25

MCO
$262
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

05/24/25

MCO
5h 23m
IAD

05/24/25

ORD
United Airlines Logo
United Airlines

05/25/25

ORD
9h 7m
IAD

05/25/25

MCO
$268
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/24/25

MCO
2h 7m
Direct

05/24/25

ORD
American Airlines Logo
American Airlines

05/25/25

ORD
3h 50m
Direct

05/25/25

MCO
$275
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/21/25

MCO
7h 34m
JFK

05/21/25

ORD
JetBlue Logo
JetBlue

05/25/25

ORD
7h 24m
JFK

05/25/25

MCO
$278
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/24/25

MCO
2h 5m
Direct

05/24/25

ORD
American Airlines Logo
American Airlines

05/28/25

ORD
6h 48m
PHL

05/28/25

MCO
$287
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

MCO
2h 7m
Direct

05/25/25

ORD
American Airlines Logo
American Airlines

05/31/25

ORD
6h 34m
CLT

05/31/25

MCO
$287
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

MCO
2h 7m
Direct

05/25/25

ORD
American Airlines Logo
American Airlines

05/31/25

ORD
8h 40m
DCA
CLT

06/01/25

MCO
$297
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/23/25

MCO
5h 18m
MIA

05/23/25

ORD
American Airlines Logo
American Airlines

05/31/25

ORD
3h 50m
Direct

05/31/25

MCO
$311
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/22/25

MCO
5h 51m
MIA

05/22/25

ORD
American Airlines Logo
American Airlines

05/28/25

ORD
3h 50m
Direct

05/28/25

MCO
$311
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/24/25

MCO
6h 9m
DCA

05/24/25

ORD
American Airlines Logo
American Airlines

05/28/25

ORD
8h 17m
DCA

05/28/25

MCO
$326
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

05/03/25

MCO
5h 21m
IAH

05/03/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/06/25

ORD
7h 39m
DFW

05/06/25

MCO
$330
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/25/25

MCO
7h 3m
CLT
PHL

05/25/25

ORD
American Airlines Logo
American Airlines

05/31/25

ORD
8h 38m
MIA

05/31/25

MCO
$337
Free cancellation within 83 hours of booking

Top Deals on flights from Orlando to Chicago O Hare Airport

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

Frontier Airlines Logo
Frontier Airlines

May 17

MCO
2h 9m
Direct

May 17

ORD

as low as

$47

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

Spirit Airlines Logo
Spirit Airlines

Jun 3

MCO
2h 8m
Direct

Jun 3

ORD

as low as

$54

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

 Logo

Jun 10

MCO
2h 8m
Direct

Jun 10

ORD

as low as

$67

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

Spirit Airlines Logo
Spirit Airlines

May 21

MCO
10h 38m
ATL

May 22

ORD

as low as

$70

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

Spirit Airlines Logo
Spirit Airlines

May 19

MCO
11h 42m
DFW

May 19

ORD

as low as

$72

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

Spirit Airlines Logo
Spirit Airlines

May 20

MCO
25h 22m
FLL

May 21

ORD

as low as

$82

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

Spirit Airlines Logo
Spirit Airlines

May 28

MCO
8h 49m
LAS

May 29

ORD

as low as

$92

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

Spirit Airlines Logo
Spirit Airlines

Jun 13

MCO
3h 37m
MYR

Jun 13

ORD

as low as

$94

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

Spirit Airlines Logo
Spirit Airlines

Jun 10

MCO
11h 27m
IAH

Jun 10

ORD

as low as

$94

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

American Airlines Logo
American Airlines

Jun 10

MCO
2h 7m
Direct

Jun 10

ORD

as low as

$98

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

Frontier Airlines Logo
Frontier Airlines

May 19

MCO
5h 43m
PHL

May 19

ORD

as low as

$108

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

Delta Air Lines Logo
Delta Air Lines

Jun 7

MCO
5h 32m
ATL

Jun 7

ORD

as low as

$108

Frequently Asked Questions

What is the typical flight duration from Orlando to Chicago O Hare Airport?
The flight duration from Orlando to Chicago O Hare Airport typically ranges between 3 to 4 hours, depending on specific routes, weather conditions, and operational factors. Direct flights tend to be faster, making travel more efficient, while connecting flights could extend the journey. It’s wise to check with your airline for real-time updates and potential delays. When booking, allow some extra time for boarding procedures and security checks to ensure a smooth transition between the two cities.
Are there any direct flights from Orlando to Chicago O Hare Airport?
Yes, there are direct flights available from Orlando to Chicago O Hare Airport. Major carriers offer several nonstop options daily, which typically take between 3 to 4 hours. Availability can vary seasonally and by time of day, so it is advisable to confirm schedules when booking. Direct flights minimize travel time and complexity, offering a more straightforward journey. Additionally, pricing for these flights usually ranges from $100 to $300 one-way, depending on the time of booking and demand.
What are the best transportation options from Chicago O Hare Airport to downtown Chicago?
Travelers have several reliable transportation choices when moving from Chicago O Hare Airport to downtown Chicago. The CTA Blue Line train is an economical option, with fares typically ranging from $5 to $10, and offers a direct route to the heart of the city. Ride-sharing services such as Uber or Lyft provide door-to-door convenience at costs generally ranging from $20 to $45. Taxis and shuttle buses are also available, while renting a car can offer extra flexibility for those planning to explore beyond the downtown area.
What are the must-see attractions in Chicago for travelers arriving from Orlando?
Chicago boasts a variety of must-see attractions that capture its cultural and architectural essence. Highlights include Millennium Park with its iconic Cloud Gate, the renowned Art Institute of Chicago, and Navy Pier, which offers lakefront views and family-friendly activities. The Willis Tower Skydeck provides breathtaking cityscapes, while vibrant neighborhoods like River North offer art, dining, and boutique shopping. These attractions provide an enriching blend of historic landmarks and modern urban experiences, ensuring visitors get a well-rounded taste of the city’s diverse offerings.
Which local dishes should travelers from Orlando try when visiting Chicago?
Travelers visiting Chicago should explore its iconic culinary offerings. Be sure to try the famous Chicago-style deep-dish pizza, celebrated for its thick, buttery crust and hearty layers of cheese and tomato sauce. The Chicago-style hot dog, loaded with mustard, relish, tomatoes, and pickles, is another local staple. Additionally, Italian beef sandwiches, often dipped in savory au jus, and Garrett Popcorn provide unique flavor profiles. Each dish offers a distinct slice of the city’s rich food culture, making them a must-try for culinary enthusiasts.
What are the best family-friendly activities in Chicago for visitors from Orlando?
Chicago offers a plethora of family-friendly activities that cater to children and adults alike. The Shedd Aquarium and Field Museum present engaging educational exhibits, while the Lincoln Park Zoo offers free admission and interactive encounters with wildlife. Maggie Daley Park provides expansive outdoor play areas, including mini-golf and climbing structures, perfect for a day of family fun. The Adler Planetarium also provides immersive exhibits and shows that captivate young minds. These attractions ensure that every member of the family experiences a fun and enriching visit.
Are there any seasonal events in Chicago that travelers from Orlando should not miss?
Yes, Chicago hosts a vibrant calendar of seasonal events that should not be missed. During the summer months, events like the Taste of Chicago and Lollapalooza offer celebratory food, music, and cultural festivities, while the Chicago Air and Water Show is a spectacular visual display. In the fall, film festivals and art exhibitions provide cultural insight, and winter brings the festive charm of Christkindlmarket, featuring seasonal treats and handcrafted gifts. Checking event dates in advance is recommended to plan your visit around these unique experiences.
What are the most affordable dining options in Chicago for travelers from Orlando?
For budget-conscious travelers, Chicago provides a range of affordable dining options scattered across the city. Local diners, food trucks, and ethnic eateries in neighborhoods like Chinatown and Pilsen are popular choices, where meals typically range from $10 to $20 per person. Casual cafes and bistros near transit hubs also offer great value, ensuring you can enjoy authentic local flavors without overspending. Exploring these areas not only helps manage costs but also provides a genuine taste of the city’s diverse culinary scene.
What are the best shopping districts in Chicago for visitors from Orlando?
Chicago’s shopping scene offers diverse districts to suit every style and budget. The Magnificent Mile is famous for upscale boutiques, department stores, and luxury brands, while State Street provides a mix of high-street retailers and local shops. For a more eclectic experience, the independent boutiques and artisan markets in Wicker Park and Bucktown stand out as creative hubs. These districts are conveniently accessible by public transit and offer extensive options, helping visitors find everything from trendy fashion to unique souvenirs that capture the city’s dynamic spirit.
What are the unique cultural experiences in Chicago for travelers from Orlando?
Chicago offers a range of unique cultural experiences that reveal the city’s vibrant local heritage. Explore neighborhoods like Pilsen and Hyde Park, where colorful street art, eclectic galleries, and diverse cuisines tell the story of Chicago’s multicultural roots. Additionally, a night out in the city’s busy theater district or a live music performance in intimate jazz clubs showcases local artistry. Museums such as the Museum of Contemporary Art present innovative exhibits. These immersive experiences provide a deep dive into the creative and cultural heartbeat that distinguishes Chicago.
Is there a specific time of year when Chicago is best visited by travelers from Orlando?
While Chicago offers year-round attractions, many visitors find spring and fall to be the best times to visit. During these shoulder seasons, the weather is mild—typically ranging between 55°F and 75°F—which makes walking tours and outdoor activities more enjoyable. These periods also tend to have fewer tourists than the busy summer months, resulting in a more relaxed atmosphere and often more competitive hotel rates. Planning your trip during these times allows for comfortable sightseeing and a balanced mix of indoor and outdoor cultural experiences.
What are the health and safety precautions travelers from Orlando should be aware of in Chicago?
When visiting Chicago, it is important to follow standard health and safety precautions to ensure a comfortable stay. Be aware of personal belongings, particularly in crowded tourist areas, and keep updated on local weather conditions as temperatures can vary widely. It is also wise to review public transportation advisories and local emergency procedures before venturing out. Additionally, staying informed about current health guidelines and travel advisories can help safeguard your well-being. These measures, alongside common-sense practices, contribute to a secure and enjoyable experience.
What airport amenities are available at Chicago O Hare Airport for travelers arriving from Orlando?
Chicago O Hare Airport provides an extensive array of amenities to enhance the travel experience. Passengers can enjoy free Wi-Fi throughout the terminal areas, various comfortable lounges available with access passes, and a wide selection of retail shops and restaurants catering to different tastes and budgets. Additional conveniences such as charging stations, business centers, and clear wayfinding signage are designed to improve passenger flow. These facilities, combined with helpful information desks, ensure that travelers experience a seamless and stress-free transition upon arrival.
Are there any pet-friendly services at Chicago O Hare Airport for travelers from Orlando?
Yes, Chicago O Hare Airport offers several pet-friendly services to accommodate travelers with pets. Designated pet relief areas are available throughout the airport, ensuring that your furry companions have access to comfortable spaces during layovers or before flights. Some terminals also provide specific pet care facilities, and many airlines operating from the airport have pet-friendly policies for handling in-cabin or checked pet travel. It is advisable to review your airline’s regulations and locate these services on airport maps to ensure a smooth experience for both you and your pet.
What are the best seating options for families traveling from Orlando to Chicago?
Families traveling between the cities are advised to select seating options that prioritize comfort and convenience on board. Bulkhead seats are often recommended since they offer extra legroom and space, making it easier to manage children and carry-on items during the flight. Many airlines provide family seating arrangements or allow you to pre-select adjacent seats to keep everyone together. It is a good idea to book early to secure these preferred options. These seating selections can enhance the in-flight experience by accommodating family needs and reducing travel-related stress.