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Flight Deals from Orlando 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

Best Price. GUARANTEED.

Exclusively for Priceline Members
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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
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
2h 8m
Direct

05/23/25

ORD
Spirit Airlines Logo
Spirit Airlines

05/26/25

ORD
6h 41m
MYR

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

05/23/25

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
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
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 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
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
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
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

05/25/25

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
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

05/25/25

MCO
2h 7m
Direct

05/25/25

ORD
American Airlines Logo
American Airlines

05/28/25

ORD
5h 55m
CLT

05/28/25

MCO
$287
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

05/27/25

ORD
6h 29m
MIA

05/27/25

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 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

Jun 3

MCO
2h 8m
Direct

Jun 3

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 8m
FLL

May 20

ORD

as low as

$72

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)

American Airlines Logo
American Airlines

Jun 10

MCO
2h 14m
Direct

Jun 10

ORD

as low as

$98

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

Delta Air Lines Logo
Delta Air Lines

May 25

MCO
3h 42m
ATL

May 25

MDW

as low as

$99

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

Delta Air Lines Logo
Delta Air Lines

Jun 10

MCO
6h 38m
DTW

Jun 10

MDW

as low as

$108

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

 Logo

Jun 12

MCO
2h 10m
Direct

Jun 12

ORD

as low as

$116

Frequently Asked Questions

What is the typical flight duration from Orlando to Chicago?
The typical direct flight duration from Orlando to Chicago takes between 2.5 to 3.5 hours, though the total travel time might extend when accounting for boarding and taxiing. Connecting flights or flights with layovers could push the overall duration to between 4 to 6 hours. It’s important to note that weather conditions, air traffic, and airline scheduling can affect these times. For a smooth journey, be sure to check the latest flight status and allow additional time for check-in procedures.
Are there any direct flights from Orlando to Chicago?
Yes, there are direct flights available from Orlando to Chicago. These flights typically take between 2.5 to 3.5 hours, offering a quicker option compared to flights with layovers. Travelers are encouraged to compare schedules and prices as airlines often offer multiple direct routes throughout the day. Booking in advance can secure better seating and fare deals, and checking any in-flight amenities is beneficial to ensure a comfortable trip, especially if traveling with families or in groups.
What are the best transportation options from Chicago airport to downtown or popular attractions?
There are several practical transportation options available from Chicago airports. The CTA Blue Line provides an economical choice with fares typically ranging from $5 to $7, while taxis and rideshare services like Uber or Lyft offer convenience with prices generally between $30 to $50, depending upon traffic conditions. Additionally, airport shuttles and rental cars offer flexibility if planning multiple stops. Ensure you check schedules and estimated trip durations ahead of time for a seamless transit from the airport to downtown and various attractions.
What are the must-see attractions in Chicago for travelers arriving from Orlando?
For first-time visitors arriving from Orlando, Chicago boasts a variety of must-see attractions that offer a rich cultural and architectural experience. Iconic landmarks such as Millennium Park, Willis Tower, and Navy Pier combine art, history, and entertainment. Unique museums like The Art Institute and interactive family zones provide additional variety. Exploring local neighborhoods or enjoying a river cruise can reveal hidden gems. It’s wise to plan your itinerary in advance and allocate additional time for unexpected discoveries while exploring this vibrant destination.
Which local dishes should travelers from Orlando try when visiting Chicago?
Travelers are encouraged to sample Chicago’s renowned culinary delights. Iconic dishes include the deep-dish pizza with its thick, buttery crust and hearty toppings, as well as the famous Chicago-style hot dog, known for its unique toppings and mustard. Italian beef sandwiches also represent a local favorite. In addition, seasonal farm-to-table specials and diverse ethnic eateries reflect the city’s cultural melting pot. Dining experiences range from casual eateries priced between $10 to $20 per meal, to upscale restaurants offering a more refined taste.
What are the best family-friendly activities in Chicago for visitors from Orlando?
Visitors will find an abundance of family-friendly activities to explore. Top choices include interactive museums like the Field Museum and the Shedd Aquarium, where educational exhibits engage visitors of all ages. Millennium Park offers open spaces for relaxation and outdoor events, while Navy Pier features amusement rides and boat tours suited for families. Additionally, local festivals and seasonal events provide enriching experiences. These activities generally range in cost from free to moderate entry fees between $15 and $35, making them accessible for various budgets.
Are there any seasonal events in Chicago that travelers from Orlando should not miss?
Yes, Chicago hosts several seasonal events that provide a unique cultural experience. In the spring and summer, events like the Chicago Blues Festival and various neighborhood festivals highlight local art and music. Fall brings food festivals and cultural parades, while winter is known for ice skating at Millennium Park and holiday markets. Each season offers different attractions, so reviewing the local event calendar before travel can help you plan around these festivities. This varied programming allows visitors to enjoy vibrant local traditions year-round.
What are the most affordable dining options in Chicago for travelers from Orlando?
Travelers will find an array of affordable dining options throughout Chicago. Neighborhood diners, food trucks, and local pizzerias offer hearty meals typically ranging from $10 to $20 per person. Ethnic eateries provide flavorful options at budget-friendly prices, while casual cafes and sandwich shops allow for quick meals without compromising quality. Look out for lunch specials and happy hour menus for additional savings. These options not only keep costs manageable but also offer an authentic taste of Chicago’s diverse food scene.
What are the best shopping areas in Chicago for souvenirs that travelers from Orlando should explore?
Chicago offers a variety of shopping experiences, ideal for picking up unique souvenirs and memorabilia. The Magnificent Mile is renowned for its mix of high-end retailers and local boutiques, while shopping districts near Navy Pier and the Riverwalk provide artisan crafts and specialty items. Additionally, local markets and pop-up shops often feature locally made jewelry, art, and vintage finds. Budget considerations and personal style can guide you to the perfect spot. Always compare prices and verify authenticity to ensure a satisfying shopping experience.
What are the customs requirements for travelers flying from Orlando to Chicago?
Since both Orlando and Chicago are located within the United States, standard customs requirements do not apply to this domestic journey. Instead, travelers must adhere to TSA security protocols and carry acceptable identification, such as a driver’s license or passport. It is advisable to arrive early at the airport to allow sufficient time for security screening. Keeping informed about any updates in airline or airport policies can help ensure a smooth experience from check-in through boarding.
Is there a specific time of year when Chicago is best visited by travelers from Orlando?
Visiting during the spring and early fall is often recommended, as these seasons provide mild temperatures and fewer crowds, especially when compared to the extreme winter cold or the busy summer season. The comfortable weather enhances outdoor activities and sightseeing opportunities, allowing visitors to enjoy parks, festivals, and culinary tours. Planning your trip in these shoulder seasons can also result in more affordable travel and hotel rates. However, each season offers its unique charm, so consider your interests and desired activities when scheduling your visit.
What are the best seating options for families traveling from Orlando to Chicago?
Family travelers should consider booking seats that offer extra legroom or bulkhead seating, which can provide additional space for children and easier access to storage. Many airlines offer family-preferred seating configurations, allowing parents to sit together or near aisle exits for convenience. Booking in advance can secure these seats, and choosing seats closer to the front of the cabin can reduce boarding time. It is advisable to check the airline’s seating policy and any available upgrades to ensure a comfortable journey for all family members.
Are there any health precautions travelers from Orlando should be aware of when visiting Chicago?
Yes, travelers should consider some health precautions when visiting Chicago. The city’s weather can vary significantly, so dressing in layers is essential, especially during transitional seasons. It is wise to carry basic medications and sunscreen, and remain informed about any local health advisories, such as seasonal flu outbreaks or air quality concerns. Additionally, verify that your travel insurance covers any potential medical needs. Always practice good hygiene, and check the latest travel health updates before departure to ensure a safe trip.
What unique airport amenities can travelers expect in Chicago upon arrival from Orlando?
Travelers arriving in Chicago can enjoy a wide range of unique airport amenities. Major hubs in the area often feature art installations, live music, and curated dining experiences that reflect the city’s cultural vibe. Airport lounges may offer comfortable seating, workspaces, and complimentary refreshments. Free Wi-Fi, charging stations, and even relaxing wellness areas are available in many terminals. These features are designed to enhance the travel experience, providing comfort and convenience during layovers or before you begin your exploration of Chicago’s rich urban culture.
What are the best tips for first-time travelers flying from Orlando to Chicago?
For first-time travelers, preparing ahead is key. Start by planning your itinerary with a focus on Chicago’s diverse attractions, and be sure to check flight schedules and terminal maps. Arrive at the airport well in advance to account for TSA screening and potential delays. Pack smartly by including essentials such as travel documents, medications, and weather-appropriate clothing. Review seating options for added comfort, and download apps to track flights and local transit schedules. This proactive approach can greatly enhance your overall travel experience.