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Flight Deals from Orlando International Airport to Chicago 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 Midway Airport
    $163
  • Chicago O Hare Airport
    $97

Layover Airports

  • Charlotte Douglas International Airport
    $287
  • Dallas Fort Worth International Airport
    $192
  • 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
    $287
  • Myrtle Beach International Airport
    $167
  • New York John F Kennedy Airport
    $278
  • Philadelphia International Airport
    $192
  • 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

05/24/25

MCO
2h 4m
Direct

05/24/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/26/25

ORD
3h 45m
Direct

05/26/25

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
Frontier Airlines Logo
Frontier Airlines

05/08/25

MCO
1h 54m
Direct

05/08/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/12/25

MDW
3h 44m
Direct

05/12/25

MCO
$163
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
3h 39m
Direct

05/26/25

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
Frontier Airlines Logo
Frontier Airlines

05/24/25

MCO
5h 44m
DFW

05/24/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/31/25

MDW
3h 45m
Direct

06/01/25

MCO
$192
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/23/25

MCO
7h 11m
PHL

05/23/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/30/25

MDW
3h 45m
Direct

05/31/25

MCO
$192
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/24/25

MCO
5h 28m
ATL

05/24/25

MDW
Delta Air Lines Logo
Delta Air Lines

05/25/25

MDW
8h 24m
DTW

05/25/25

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

05/25/25

MCO
4h 10m
ATL

05/25/25

MDW
Delta Air Lines Logo
Delta Air Lines

05/25/25

MDW
5h 48m
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

05/25/25

ORD
6h 50m
ATL

05/25/25

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

05/05/25

MCO
4h 42m
PHL

05/05/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/12/25

MDW
3h 44m
Direct

05/12/25

MCO
$238
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
2h 7m
Direct

05/24/25

ORD
United Airlines Logo
United Airlines

05/25/25

ORD
9h 7m
IAD

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

05/30/25

ORD
7h 4m
MIA

05/30/25

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
Frontier Airlines Logo
Frontier Airlines

05/23/25

MCO
7h 11m
PHL

05/23/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/30/25

MDW
7h 26m
DFW

05/30/25

MCO
$289
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

Top Deals on flights from Orlando International Airport to Chicago

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

May 27

MCO
2h 8m
Direct

May 27

ORD

as low as

$54

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

Frontier Airlines Logo
Frontier Airlines

Jun 2

MCO
1h 55m
Direct

Jun 2

MDW

as low as

$63

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)

American Airlines Logo
American Airlines

Jun 10

MCO
2h 7m
Direct

Jun 10

ORD

as low as

$98

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

Delta Air Lines Logo
Delta Air Lines

May 24

MCO
6h 28m
DTW

May 24

MDW

as low as

$99

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

Delta Air Lines Logo
Delta Air Lines

May 25

MCO
3h 25m
ATL

May 25

MDW

as low as

$99

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

Spirit Airlines Logo
Spirit Airlines

May 24

MCO
3h 9m
MYR

May 24

ORD

as low as

$102

Frequently Asked Questions

What is the typical flight duration from Orlando International Airport to Chicago?
The typical flight duration from Orlando International Airport to Chicago usually ranges between 3 to 4 hours. Direct flights tend to be on the shorter end of that range, while connecting flights may take slightly longer due to layovers. Weather conditions and air traffic can also influence the duration. It is advisable to check your specific flight details and allow extra time for airport security and boarding procedures to ensure a smooth journey from Orlando International Airport to Chicago.
Are there any direct flights from Orlando International Airport to Chicago?
Yes, there are direct flights available from Orlando International Airport to Chicago. Airlines often offer non-stop services, which means travelers can avoid lengthy layovers. These flights usually operate with frequency throughout the week, though schedules may vary seasonally. Booking in advance may help secure better fares and preferred timings. It’s a good idea to review current flight schedules as changes can occur based on demand and operational adjustments, ensuring a seamless travel experience between the two cities.
What are the best transportation options from Chicago airport to downtown or popular attractions?
For transportation from Chicago airports to downtown or popular attractions, travelers can consider several dependable options. The CTA Blue or Orange Line trains provide fast and economical transit for around $4 to $8 per ride. Additionally, taxis and rideshares like Uber or Lyft typically cost between $20 and $50 depending on traffic and time of day. Shuttle services and rental cars are also available, though parking downtown may be limited. Checking current schedules and traffic conditions ahead of time ensures a hassle-free journey after landing.
What are the must-see attractions in Chicago for travelers arriving from Orlando?
Chicago boasts numerous must-see attractions ideal for visitors from Orlando. Highlights include Millennium Park, home to the iconic Cloud Gate sculpture, and Navy Pier, which offers entertainment and scenic lake views. The Art Institute of Chicago features world-class art collections, while the Willis Tower Skydeck provides breathtaking city panoramas. Exploring the Chicago Riverwalk and Lincoln Park Zoo also adds to the experience. These attractions offer a rich mix of culture, architecture, and outdoor fun, making them essential stops during your Chicago visit.
Which local dishes should travelers from Orlando try when visiting Chicago?
Travelers arriving in Chicago should sample its renowned culinary offerings. A deep-dish pizza with a buttery, flaky crust topped with rich tomato sauce and cheese is a must-try, as are Italian beef sandwiches served with sweet or hot giardiniera. Chicago-style hotdogs and creative fusion dishes in local diners also reflect the city's vibrant food scene. Many eateries in various neighborhoods offer these dishes at competitive prices, allowing a taste of Chicago’s iconic flavors that offer a distinctly different experience from what you might find in Orlando.
What are the best family-friendly activities in Chicago for visitors from Orlando?
Chicago provides a variety of family-friendly activities suitable for visitors from Orlando. Educational institutions like the Field Museum, Shedd Aquarium, and Adler Planetarium offer interactive exhibits and animal encounters ideal for kids. Outdoor spaces such as Millennium Park and Maggie Daley Park provide ample opportunities for play and picnics. Additionally, scenic boat tours along the Chicago River give families a unique perspective of the city's architecture. These activities, coupled with many hands-on museums and local parks, ensure an engaging and memorable experience for families during their stay.
Are there any seasonal events in Chicago that travelers from Orlando should not miss?
Yes, Chicago hosts an array of seasonal events that visitors traveling from Orlando should consider. Winter brings festive holiday markets, ice skating at Millennium Park, and special cultural performances, while summer features the Taste of Chicago food festival, outdoor concerts, and architectural boat tours. Spring sees garden festivals and neighborhood cultural celebrations that highlight local art and cuisine. Ticket prices can range from free admission events to moderately priced festivals. Checking the event calendar before your trip can help you plan and take full advantage of these unique seasonal happenings.
What are the most affordable dining options in Chicago for travelers from Orlando?
Chicago offers a wide range of affordable dining options that cater to budget-savvy travelers. Food trucks, local diners, and casual eateries throughout the city serve classic Chicago-style hotdogs, deep-dish pizzas, and hearty sandwiches at prices ranging from $8 to $15 per meal. Neighborhood cafes and ethnic restaurants also provide a variety of cuisines at moderate prices, usually between $10 and $20 per dish. Exploring dining districts outside the major tourist hubs can reveal hidden gems with authentic local flavors, ensuring that your dining experience is both delightful and economical.
What are the best shopping districts in Chicago for travelers from Orlando?
Chicago offers several shopping districts that cater to diverse tastes and budgets. The Magnificent Mile on Michigan Avenue is popular for its upscale brands and flagship stores, while neighborhoods like Wicker Park and Bucktown offer trendy boutiques and vintage shops. These areas provide options ranging from affordable fashion finds at around $20 per item to luxury brands with premium pricing. Exploring these districts not only offers a chance to shop but also provides a taste of the local cultural and architectural ambiance, making the experience enjoyable and distinctly different from shopping options available in Orlando.
What cultural tips should travelers from Orlando keep in mind when visiting Chicago?
Travelers should be aware that Chicago is a melting pot of cultures, and courtesy is highly valued. When dining in local restaurants, tipping between 15% and 20% is standard practice. It’s also a good idea to familiarize yourself with local slang and community norms, especially in neighborhoods with rich ethnic identities. Public transportation etiquette, like offering seats to those in need, will be appreciated by locals. Engaging with residents for dining or cultural recommendations can enhance your experience, ensuring a respectful and enriched visit while you enjoy Chicago’s vibrant lifestyles.
What are the best car rental options in Chicago for travelers from Orlando?
Chicago’s car rental market offers a variety of services ideal for visitors from Orlando. Major companies like Enterprise, Avis, and Hertz provide competitive rates, typically ranging from $40 to $100 per day depending on the rental duration and seasonal demand. Many rental facilities are located at both major airports and central areas, offering flexible pick-up and drop-off options. Additional features such as GPS, child seats, and insurance packages can be added for convenience. It is advisable to compare rates online and book in advance to secure the best deal while considering downtown traffic and parking challenges.
Is there a specific time of year when Chicago is best visited by travelers from Orlando?
Yes, travelers find that spring (April to June) and early fall (September to October) offer the most pleasant conditions in Chicago. During these periods, the weather is mild—usually ranging from 60°F to 75°F—and the crowds are thinner compared to peak summer. The transitional seasons allow for comfortable sightseeing, outdoor dining, and participation in various cultural events, all while avoiding the extremes of winter chills or summer heat. However, each season in Chicago offers its own unique charm, so plan according to your interests and tolerance for weather conditions.
What are the customs requirements for travelers flying from Orlando to Chicago?
This information is not applicable to Chicago or Orlando because both are within the United States and do not require customs procedures for domestic flights. Travelers only need a valid government-issued photo ID to pass through TSA security checkpoints at both terminals. While customs are mandatory for international travel, the process for domestic flights is straightforward, simplifying your transition between these two cities. Always confirm any updates from your airline or airport, but generally, the experience remains efficient and stress-free when flying domestically.
Are there any unique airport amenities in Chicago for travelers arriving from Orlando?
Chicago airports, especially O’Hare International, feature a variety of unique amenities designed for traveler comfort. Passengers can enjoy diverse dining venues offering local Chicago cuisine, along with upscale retreats like VIP lounges and wellness areas. Free Wi-Fi, art exhibits, and interactive installations enhance the waiting experience, reflecting the city’s cultural vibrancy. Additionally, services such as expedited security, premium lounges with spa treatments, and extensive retail options elevate the overall airport experience. These amenities help create a welcoming atmosphere, making your arrival in Chicago both convenient and enjoyable.
What are the best seating options for families traveling from Orlando to Chicago?
Airlines offer several seating options that cater specifically to families traveling from Orlando to Chicago. Options include bulkhead seats and seats with extra legroom, which can provide additional space for children and carry-ons. Some carriers also offer family seating arrangements to ensure adjacent seating for a more comfortable experience. When booking, ask about options like premium economy upgrades or exit row seats if available, although these may come at an additional cost ranging from $10 to $30 extra. Confirm seating preferences early to secure the best configuration for your family’s needs during the flight.