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Cheap Flights from Orlando (SFB) to Chicago (CHIA)

Compare Orlando Sanford to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Orlando Sanford to Chicago

Looking for a cheap last-minute deal or the best return flight from Orlando Sanford Airport to Chicago? If you want to travel next month, return fares start from $212. Find the lowest prices on one-way and return tickets right here.
Chicago.$139 per passenger.Departing Wed, 28 Oct, returning Mon, 9 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Wed, 28 Oct, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 9 Nov, arriving in Orlando Sanford.Price includes taxes and charges.From $139, select.
Chicago.$149 per passenger.Departing Fri, 6 Nov, returning Mon, 9 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 6 Nov, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 9 Nov, arriving in Orlando Sanford.Price includes taxes and charges.From $149, select.
Chicago.$150 per passenger.Departing Fri, 11 Sep, returning Fri, 18 Sep.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 11 Sep, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 18 Sep, arriving in Orlando Sanford.Price includes taxes and charges.From $150, select.
Chicago.$169 per passenger.Departing Wed, 7 Oct, returning Mon, 19 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Wed, 7 Oct, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 19 Oct, arriving in Orlando Sanford.Price includes taxes and charges.From $169, select.
Chicago.$190 per passenger.Departing Mon, 7 Dec, returning Mon, 14 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Mon, 7 Dec, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 14 Dec, arriving in Orlando Sanford.Price includes taxes and charges.From $190, select.
Chicago.$191 per passenger.Departing Fri, 22 Jan, returning Mon, 25 Jan.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 22 Jan, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 25 Jan, arriving in Orlando Sanford.Price includes taxes and charges.From $191, select.
Chicago.$203 per passenger.Departing Mon, 31 Aug, returning Fri, 18 Sep.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Mon, 31 Aug, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 18 Sep, arriving in Orlando Sanford.Price includes taxes and charges.From $203, select.
Chicago.$212 per passenger.Departing Fri, 28 Aug, returning Mon, 31 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 28 Aug, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 31 Aug, arriving in Orlando Sanford.Price includes taxes and charges.From $212, select.
Chicago.$216 per passenger.Departing Fri, 25 Sep, returning Mon, 12 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 25 Sep, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 12 Oct, arriving in Orlando Sanford.Price includes taxes and charges.From $216, select.
Chicago.$266 per passenger.Departing Fri, 22 Jan, returning Mon, 1 Feb.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 22 Jan, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 1 Feb, arriving in Orlando Sanford.Price includes taxes and charges.From $266, select.
Chicago.$268 per passenger.Departing Tue, 29 Dec, returning Mon, 18 Jan.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Tue, 29 Dec, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Mon, 18 Jan, arriving in Orlando Sanford.Price includes taxes and charges.From $268, select.
Chicago.$332 per passenger.Departing Mon, 16 Nov, returning Fri, 4 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Mon, 16 Nov, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 4 Dec, arriving in Orlando Sanford.Price includes taxes and charges.From $332, select.
Chicago.$347 per passenger.Departing Fri, 31 Jul, returning Fri, 7 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Fri, 31 Jul, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 7 Aug, arriving in Orlando Sanford.Price includes taxes and charges.From $347, select.
Chicago.$538 per passenger.Departing Wed, 29 Jul, returning Fri, 31 Jul.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Orlando Sanford on Wed, 29 Jul, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Fri, 31 Jul, arriving in Orlando Sanford.Price includes taxes and charges.From $538, select.

Find the cheapest month to fly from Orlando Sanford to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Orlando Sanford to Chicago flights are currently cheapest in November.
Jul
from $538
Aug
from $212
Sep
from $150
Oct
from $169
Nov
from $149
Dec
from $190
Jan
from $191
Feb
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Mar
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Apr
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May
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Jun
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Direct flights from Orlando Sanford to Chicago

Alternative Orlando Sanford to Chicago routes

Looking for the cheapest, fastest or easiest route from Orlando Sanford to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
Closest
from $352
Search flights

Chicago O'Hare International

25km from central Chicago
from $552
Search flights

Chicago Rockford

127km from central Chicago
Cheapest
from $139
Search flights

Orlando to Chicago: Flight information

The things to know before you go.
Cheapest flight found$139
Cheapest month to flyOctober
Average flight time2 hrs, 50 mins
Most popular airlineAllegiant Air
Average flights per week4

Finding cheap flights from Orlando Sanford to Chicago: Frequently asked questions

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
The best price we found for a return flight from Orlando Sanford to Chicago is $139. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 50 minutes is the average flight time from Orlando Sanford to Chicago.
Allegiant Air flies direct from Orlando Sanford to Chicago.
As of July 2026, there are 4 flights per week flying from Orlando Sanford to Chicago.
The cheapest month to fly from Orlando Sanford to Chicago is usually October.
If you're flying from Orlando Sanford Airport, the cheapest airport near Chicago is Chicago Rockford – which is 126.5 km away from the centre of Chicago. We've found flights into this airport from $139.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Orlando Sanford Airport to Chicago on Wednesday, 28 October 2026.
Yes – the average flight time is 2 hours and 50 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

In July, the average temperature is usually around 22°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Allegiant Air offers the cheapest flight tickets to Chicago.

Flying from Orlando Sanford International Airport (SFB) to Chicago: what you need to know

  • Orlando Sanford International Airport is located in Orlando. Following the UTC-6 timezone, Chicago is one hour behind Orlando.

  • The most popular route is from Orlando Sanford International Airport (SFB) to Chicago Rockford International Airport (RFD). There are two weekly services between these two airports. If you want to get on your way as soon as you can, the earliest flight from SFB to RFD is the 06:00 Allegiant Air service. If you prefer to leave later in the day, the final departure is at 17:40 with Allegiant Air.

  • For hassle-free travel, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This leaves you with plenty of time to board your SFB to Chicago flight.

  • Flying during a peak time such as June? Major public holidays and other popular periods can mean longer queues at security. Play it safe and arrive up to four hours ahead of an international flight and two hours before domestic departures.

  • Direct Orlando Sanford International Airport to Chicago tickets are available for booking. Chicago Rockford International Airport (RFD) is where you'll complete your journey.

  • Book your ticket with Allegiant Air. This leading carrier operates direct flights from Orlando Sanford International Airport to Chicago.

  • SFB is about 31 kilometres from central Orlando. If you're ride-sharing, driving or catching a taxi from the centre, it'll take you 35 minutes or so to get there, depending on the traffic. If you're taking public transport, expect the travel time to be around 1 hour.

  • Want a relaxed start to your travels? Stay near SFB. Whether you're catching an early flight from Orlando Sanford International Airport to Chicago or just don't want to be rushed, these hotels put convenience first:

  • 69% of flights that take off from Orlando Sanford International Airport make it to their destination on schedule.

How to find the cheapest flights from Orlando Sanford International Airport (SFB) to Chicago

  • $54 is the cheapest price we've seen for a one-way Orlando Sanford International Airport to Chicago flight. A return ticket right now is $139. Depending on when you want to go and the availability, these fares could change.

  • Booking in advance is often the key to scoring a cheap flight from SFB to Chicago. Fares tend to rise as demand increases, so the closer you get to departure, the more it could cost you.

  • The 'Whole month' search tool will show you the cheapest tickets from Orlando Sanford International Airport to Chicago across the entire month. It's a great way to find a bargain if your trip dates are flexible.

  • Snapping up a cheap flight from SFB to Chicago is easy with Price Alerts. All you need to do is set up one of these automatic notifications and we'll notify you when there's a better deal.

  • Tailor your trip with filters. Choose your ideal arrival and departure times, total journey duration and airlines. You can also sort the results by 'Cheapest,' 'Best' or 'Fastest' flights from Orlando Sanford International Airport to Chicago.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

  • Chicago O'Hare International Airport (ORD) is around 27 kilometres from central Chicago. If you're opting for a ride-share or a taxi, the drive will take roughly 30 minutes.

  • It takes around 45 minutes if you're travelling on public transport.

  • If you have a late flight from Orlando Sanford International Airport to Chicago, few things beat the convenience of staying close to the terminal. Collect your bags from the carousel and then be showered and resting not long after at one of these accommodation options near ORD:

  • Booking your ride from Chicago O'Hare International Airport around four weeks before your flight from SFB to Chicago can help you get the best possible rate.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • After your flight from Orlando Sanford International Airport to Chicago has arrived, you can make your way to the city centre in around 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).

  • If you're travelling on public transport, it'll take about 30 minutes.

  • Hang up the 'Do not disturb' sign and unwind at a hotel near MDW. Here are a few options where you can kick back after your SFB to Chicago flight:

  • Avoid paying extra. Securing your ride four weeks before your arrival at MDW can get you a lower rate.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from Orlando Sanford International Airport to Chicago and make your way to your hotel or start exploring right away. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 40 minutes to reach driving.

  • If you travel by public transport, the journey time is about 2 hours.

  • If you don't want to make the trip to the centre, find a hotel close to RFD. Make yourself comfortable at one of these stays after your SFB to Chicago flight:

  • Rental agencies sometimes offer discounts on early bookings, so secure your vehicle from RFD a few weeks ahead of your flight from Orlando Sanford International Airport to Chicago. A little prep today saves cash tomorrow.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • July is the most popular month for flights from Orlando Sanford International Airport to Chicago. To escape the crowds, plan your trip to Chicago in January.

  • Lock in a Orlando Sanford International Airport to Chicago plane ticket with a departure in July to explore the city during its warmest month. Expect temperatures to range from 16ºC (61ºF) to 28ºC (82ºF).

  • Search for cheap tickets from SFB to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

  • Start your Chicago trip off on the right foot by choosing the perfect place to stay. Once you've booked your flight from Orlando Sanford International Airport to Chicago, explore our selection of hotels including:

  • There are so many things to explore in this city it can be hard to know where to begin. Art Institute of Chicago, Millennium Park and Willis Tower are highlights which should feature on every Chicago itinerary.

Explore more of the United States

  • Columbus is just one of the many cities in the United States waiting to be explored once you've seen Chicago. Around 451 kilometres away to the southeast, well-known attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

  • If you're interested in discovering another side of the United States, consider Indianapolis, about 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among its highlights.

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Prices shown on this page are estimated lowest prices only. Found in the last 12 days.