Flights from Orlando to Chicago, United States

Select sites to compare prices |
  • Select all
  • Deselect all

Find Flights


Enter your destination to continue
Enter depart date to continue
Enter return date to continue
Select at least 3 sites to continue
Select your depart date
Select your return date
Location services timed out
Enable Location Services Required!
Location services not available at this time
Use current location
Did you mean flights from Chicago to Orlando?

Orlando to Chicago Last modified: Mar 24, 2019 3:10 -04:00

We've scanned 48,195,047,545 round trip itineraries and found the cheapest flights to Chicago. United & Spirit frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

Wed 4/17
Wed 4/24
Tue 4/16
Tue 4/23
Fri 5/17
Sat 5/18
Wed 4/17
Sat 4/20
Wed 5/8
1 stop
Tue 5/14
1 stop
Tue 4/9
1 stop
Wed 4/17
1 stop

How Much is a Flight from Orlando to Chicago?

We have collected flight cost data from across the web for travel from Orlando to Chicago, and have found the average flight price for this trip to be $140.

Where To Buy Cheap Flights from Orlando to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Orlando to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Orlando to Chicago?

The chart below shows up-to-date information regarding how far in advance to book your flight from Orlando to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $147 $255
7-14 days $184 $228
14-21 days $142 $158
21-30 days $97 $149
30-60 days $133 $135
60-90 days $151 $168
90+ days $147 $179

Cheapest Day To Fly from Orlando to Chicago

We've examined 57,595,778,181 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Orlando to Chicago is Wednesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday

Compare Flight Prices from Orlando to Chicago by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Orlando to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
March Orlando Chicago United 3/27/19 4/2/19 0 $147
April Orlando Chicago United 4/17/19 4/24/19 0 $97
May Orlando Chicago Spirit 5/15/19 5/18/19 0 $133
June Orlando Chicago Spirit 6/4/19 6/6/19 0 $167
July Orlando Chicago American 7/23/19 8/6/19 0 $197
August Orlando Chicago Spirit 8/22/19 8/27/19 0 $147
September Orlando Chicago Spirit 9/6/19 9/10/19 0 $147
October Orlando Chicago Spirit 10/24/19 10/31/19 0 $147

Cheap Last Minute Flights from Orlando to Chicago

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Orlando to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

24 25 26 27 28 29 30
31 1 2 3 4 5 6
$353 $184
7 8 9 10 11 12 13
$184 $151
14 15 16 17 18 19 20
$151 $161
21 22 23 24 25 26 27
$161 $147
28 29 30 1 2 3 4

Connecting Flights vs Direct Flights from Orlando to Chicago

Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Orlando to Chicago is $218.

The average price for direct flights from Orlando to Chicago is $187.

The chart below shows up to date information regarding non-stop flights from Orlando to Chicago.

Weekly Direct Flights from Orlando to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 5 3 4 5 5 5 5 01:43 14:11
Frontier 2 2 1 1 2 1 2 10:01 15:37
Spirit 2 2 2 2 2 2 2 01:08 10:42
United 6 6 6 6 6 6 7 02:00 11:25
Major Airlines 7 7 7 7 7 9 7 01:20 17:55

One Way Flights vs Round Trip Flights from Orlando to Chicago

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Orlando to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Orlando to Chicago is $80.

The average price for round trip flights from Orlando to Chicago is $181.

Orlando to Chicago Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is the flight from Orlando to Chicago?
Answer: The average Orlando to Chicago flight time is 2 hours and 57 minutes.
Question: How far is Chicago from Orlando?
Answer: The distance from Orlando to Chicago is 990 miles (1,593 kilometers).
Question: How common are direct flights from Orlando to Chicago?
Answer: There are 150 direct flights from Orlando to Chicago.
Question: What are the most popular Orlando airlines for direct flights from Orlando to Chicago?
Answer: Major Airlines provides 34% of the non-stop flights between Orlando and Chicago.
Question: What are the most popular connecting cities when flying from Orlando to Chicago?
Answer: Atlanta, GA

Airlines in Orlando flying to Chicago Last modified: Mar 24, 2019 3:10 -04:00Number of routes searched: 365Number of itineraries searched: 2,888,265

Wondering which airlines fly out of Orlando to Chicago? We've gathered the average price of Orlando airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

Orlando to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
Major Airlines -
Frontier -
Allegiant Air -
Spirit -
United -
American CLT
American DCA
American DFW
American JFK
Alaska PDX
Alaska SAN
Alaska SEA
Alaska SFO
JetBlue BOS
JetBlue JFK
JetBlue SJU
Major Airlines ATL
Major Airlines DTW
Major Airlines MSP
Major Airlines CVG
Frontier DEN
Frontier LAS
Spirit ATL
Spirit AUS
Spirit BOS
Spirit BWI
Sun Country MSP
United CLE
United DEN
United EWR
United EYW

Orlando to Chicago Airports

These are the major commercial airports we're currently monitoring in Orlando and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

We are updating our Cookie Policy. FareCompare will use cookies and other tracking technologies to assist with navigation and product selection, analyze your use of our services, assist with our promotional and marketing efforts, and provide deals content from third parties.

Cheap Flights from Orlando to Chicago