Cheap flights from Orlando to Chicago

Orlando Executive
ORL
Chicago FSS
CHI

Flight deals from Orlando to Chicago

Below you can see the best deals on flights Orlando — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 9 September, from $53.

Top 10 cheap flights from Orlando to Chicago

F9
$ 54

Orlando — Chicago

20:51—22:59
9 Sep 2026
3 h 8 m
Direct flight
F9
$ 58

Orlando — Chicago

21:00—23:08
5 Sep 2026
3 h 8 m
Direct flight
F9
$ 58

Orlando — Chicago

20:51—22:59
12 Sep 2026
3 h 8 m
Direct flight
F9
$ 58

Orlando — Chicago

20:51—22:59
11 Sep 2026
3 h 8 m
Direct flight
F9
$ 58

Orlando — Chicago

21:00—23:08
8 Sep 2026
3 h 8 m
Direct flight
F9
$ 58

Orlando — Chicago

21:00—23:08
1 Sep 2026
3 h 8 m
Direct flight
F9
$ 58

Orlando — Chicago

21:00—23:08
2 Sep 2026
3 h 8 m
Direct flight
F9
F9
$ 66

Orlando — Chicago

09:30—11:51
14 Sep 2026
27 h 21 m
1 stop
F9
F9
$ 66

Orlando — Chicago

13:45—20:08
1 Sep 2026
7 h 23 m
1 stop
F9
F9
$ 66

Orlando — Chicago

07:57—20:08
1 Sep 2026
13 h 11 m
1 stop

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Orlando — Chicago flight

Looking for cheap flights from Orlando to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your Orlando — Chicago ticket online at the best price.

The route has direct flights — around 321 flights per week, flights are operated by United Airlines, American Airlines, Southwest Airlines, Spirit Airlines and 8 more airlines, a nonstop flight takes about 3 h 5 min, the distance between the cities is around 1,584 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $53Min. price
SeptemberCheapest
MayPeak season
YesDirect flights
1,584 kmDistance
3 h 5 minTravel time
25Airlines
321 / wkFlights

Flight schedule from Orlando to Chicago

The table shows direct flights from Orlando to Chicago on the selected date. The flight takes approximately 3 h 5 min. Regular flights are operated by United Airlines, American Airlines, Southwest Airlines and Spirit Airlines. Departures from Orlando International Airport and Orlando Sanford International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 14 Aug 2026

Flight ticket prices by day: Orlando — Chicago

Below is a calendar of the lowest flight ticket prices for Orlando — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $53 in September, and the most expensive are around $168 in May. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from Orlando to Chicago by month. Tickets are usually cheapest in February (around $169) and priciest in June (about $254) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$181lowMay$242highSep$169low
Feb$169lowJun$254highOct$181low
Mar$230highJul$254highNov$205medium
Apr$205mediumAug$218mediumDec$248high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in May. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a Orlando — Chicago ticket

  • Book ahead: fares for Orlando — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Orlando is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Chicago is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Orlando — Chicago route are operated by 12 airlines; United Airlines runs the most flights (around 23% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    24x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight MCO → ORD24x/week
      Duration
      3h 10m
      Days
      MTWTFSS
    22.7%Open →
  • American AirlinesAA
    19x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight MCO → ORD19x/week
      Duration
      3h 16m
      Days
      MTWTFSS
    18.1%Open →
  • Southwest AirlinesWN
    19x/week
    WebsiteFleet: 817140M pax/year
    • Direct flight MCO → MDW19x/week
      Duration
      2h 58m
      Days
      MTWTFSS
    • Direct flight MCO → ORD1x/week
    18.1%Open →
  • Spirit AirlinesNK
    14x/week
    WebsiteFleet: 20544.1M pax/year
    • Direct flight MCO → ORD14x/week
      Duration
      2h 51m
      Days
      MTWTFSS
    13.1%Open →
  • Frontier AirlinesF9
    9x/week
    WebsiteFleet: 15329M pax/year
    • Direct flight MCO → ORD6x/week
      Duration
      3h 10m
      Days
      MTWTFSS
    • Direct flight MCO → MDW3x/week
      Duration
      2h 59m
      Days
      MTWTFSS
    8.1%Open →
  • Alaska AirlinesAS
    4x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight MCO → ORD4x/week
    4.0%Open →
  • EmiratesEK
    2x/week
    WebsiteFleet: 26051.9M pax/year
    • Direct flight MCO → ORD2x/week
      Duration
      1h
      Days
      MTWTFSS
    2.2%Open →
  • Air New ZealandNZ
    2x/week
    WebsiteFleet: 10816M pax/year
    • Direct flight MCO → ORD2x/week
      Duration
      1h
      Days
      MTWTFSS
    1.9%Open →
  • Air CanadaAC
    2x/week
    WebsiteFleet: 20346M pax/year
    • Direct flight MCO → ORD2x/week
    1.9%Open →
  • IberiaIB
    1x/week
    WebsiteFleet: 9224M pax/year
    • Direct flight MCO → ORD1x/week
    1.2%Open →
  • British AirwaysBA
    1x/week
    WebsiteFleet: 29243M pax/year
    • Direct flight MCO → ORD1x/week
    0.9%Open →
  • Copa AirlinesCM
    1x/week
    WebsiteFleet: 10316.1M pax/year
    • Direct flight MCO → ORD1x/week
    0.9%Open →

Cities and airports on the Orlando — Chicago route

Flights Orlando — Chicago depart from Orlando International Airport and Orlando Sanford International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Orlando

ORL
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the Orlando — Chicago flight

How long is the flight from Orlando to Chicago?

A nonstop Orlando — Chicago flight takes about 3 h 5 min — the distance between the cities is around 1,584 km.

How far is it from Orlando to Chicago?

The distance from Orlando to Chicago is about 1,584 km, which a nonstop flight covers in around 3 h 5 min.

Are there direct flights from Orlando to Chicago?

Yes, there are nonstop flights Orlando — Chicago — around 321 flights per week.

Which airlines fly from Orlando to Chicago?

Airlines operating Orlando — Chicago include United Airlines, American Airlines, Southwest Airlines, Spirit Airlines, Frontier Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Orlando — Chicago flights use?

Flights from Orlando depart from Orlando International Airport, Orlando Sanford International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Orlando to Chicago?

The price of a Orlando — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in May. Tickets typically cost between $53 and $168. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Orlando — Chicago?

Flights Orlando — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Orlando to Chicago?

To catch a low fare Orlando — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Orlando

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New York CityAtlantaWashington, D.C.DallasSan JuanCharlottePhiladelphiaBostonHoustonMiamiLos AngelesFort LauderdaleDetroitTorontoDenverNashvilleSeattleBogotaRaleighNew OrleansSan FranciscoPanama CityAustinMinneapolisSalt Lake CityClevelandLondonSan DiegoMexico CityLas VegasIndianapolisHartfordSao PauloPhoenixMontrealSanto DomingoPunta CanaPittsburghNorfolkColumbus

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochesterCleveland

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