good.flights

Cheap flights from Orlando to Chicago

One-way from $51, found by travellers in the last 7 days. Aviasales checks the live price.

Departure
Return
Prices for nearby dates
Tue, Oct 20Any priceWed, Oct 21Any priceThu, Oct 22$118Fri, Oct 23$51Sat, Oct 24Any priceSun, Oct 25Any priceMon, Oct 26Any priceTue, Oct 27Any price

Cheapest one-way tickets

Recent finds on different dates, for 1 adult. Baggage and fare rules are shown on Aviasales, where the price is checked live.

Cheapest
$51
Allegiant Air, flight G4 1319Found 4 days ago, 1 adult
Check price on Aviasales
6:10amOrlandoFri, Oct 23
Travel time 2h 44m, nonstopSFBRFD
7:54amChicagoFri, Oct 23
$56
Frontier Airlines, flight F9 1563Found 4 days ago, 1 adult
Check price on Aviasales
7:04amOrlandoTue, Nov 3
Travel time 4h 14m, 1 stopMCOORD
10:18amChicagoTue, Nov 3
$93
Allegiant Air, flight G4 1344Found 3 days ago, 1 adult
Check price on Aviasales
7:00amOrlandoWed, Oct 7
Travel time 2h 44m, nonstopSFBRFD
8:44amChicagoWed, Oct 7
$100
Allegiant Air, flight G4 2922Found 5 days ago, 1 adult
Check price on Aviasales
6:20amOrlandoFri, Oct 9
Travel time 2h 42m, nonstopSFBRFD
8:02amChicagoFri, Oct 9
$101
Frontier Airlines, flight F9 1563Found 3 days ago, 1 adult
Check price on Aviasales
7:01amOrlandoWed, Mar 3
Travel time 4h 22m, 1 stopMCOORD
10:23amChicagoWed, Mar 3

Round trips

The cheapest return tickets found recently, price for the whole trip.

Plan the rest of the trip

  • Mobile data in United StatesTravel eSIM from $4, installed before you fly.
    Compare plans
  • Getting from the airportTransfers and car hire in Chicago, booked ahead at a fixed price.
    See options
  • Things to do in ChicagoPopular tours from $27.95 per person.
    See ideas
  • Flight delayed?Delayed or cancelled? See which passenger rights cover this route.
    Check

Price calendar

The lowest one-way fare found for each day over the next 60 days. A dash means no recent fare; you can still pick that day.

October 2026

MoTuWeThFrSaSu1234$2355$1476–7$938$1429$10010$10211–12–13–14–15–16–17–18–19$13320–21–22$11823$5124–25–26–27–28–29–30–31–

November 2026

MoTuWeThFrSaSu1–2–3$564–5–6–7–8–9–10–11–12–13–14–15–16–17–18–19–20–21–22–23–24–25–26–27–28–29–30–

December 2026

MoTuWeThFrSaSu1–2–345678910111213141516171819202122232425262728293031
$93 or lessGreen: the cheapest fifth of fares on this route. Lowest in these 60 days: Oct 23, $51.

Lowest fares by month

In the fares found this week, October has the lowest: from $51 one-way, against $126 in December. Pick a month to see its cheapest date.

$0$50$100$150$51OctNovDecJanFebMarAprMayJunJulAugSep
Show as a table
MonthCheapest one-wayDateStops
October$51Fri, Oct 23Nonstop
November$56Tue, Nov 31 stop
December$126Wed, Dec 30Nonstop
January 2027—
February 2027—
March 2027$101Wed, Mar 31 stop
April 2027—
May 2027—
June 2027—
July 2027—
August 2027—
September 2027—

Questions travellers ask

What is the cheapest month to fly from Orlando to Chicago?

In the fares found this week, October has the lowest: from $51 one-way, against $126 in December.

Are there direct flights from Orlando to Chicago?

Yes. Recent fares include nonstop flights with Allegiant Air and Frontier Airlines.

How long is the flight from Orlando to Chicago?

A nonstop flight takes about 2h 42m. The distance is 1,006 mi.

More cheap flights from Orlando

All 174 destinations