Orlando to Chicago MCO, SFB → MDW, ORD, RFD
Orlando International Airport (MCO), Orlando Sanford International Airport (SFB) → Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD)
The cheapest return found recently is $130 with Allegiant Air, 6 Nov – 9 Nov, found yesterday. The cheapest one-way found recently is $67 with Frontier Airlines, 2 Dec, found today.
Return
The cheapest return fare on each of 9 departure dates is usually $262 to $384.
Cheapest return found recently
$130
6 Nov – 9 Nov · Allegiant Air
Orlando Sanford International Airport (SFB) → Chicago Rockford International Airport (RFD)
Leaves 6:50 a.m. · Return leaves 10:38 a.m. · 5 h 24 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Cheapest nonstop return
$130
6 Nov – 9 Nov · Allegiant Air
Orlando Sanford International Airport (SFB) → Chicago Rockford International Airport (RFD)
Leaves 6:50 a.m. · Return leaves 10:38 a.m. · 5 h 24 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Found recently, and the cheapest we hold
$130 6 Nov – 9 Novfound yesterdaySee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $119 to $161.
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 9 departure dates from 22 Oct to 29 Apr 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other 3-night return fares leaving within 3 days of 6 Nov to compare.
Every date we hold
13 fares on 9 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 22 Oct – 26 Oct | $520 | Allegiant Air | Orlando Sanford International Airport (SFB) → Chicago Midway International Airport (MDW) | out 1 stop, back 1 stop | found yesterday | See prices for these dates |
| 24 Oct – 28 Oct | $262 | Frontier Airlines | Orlando International Airport (MCO) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found today | See prices for these dates |
| 3 Nov – 9 Nov | $161 | Frontier Airlines | Orlando International Airport (MCO) → O'Hare International Airport (ORD) | out 1 stop, back nonstop | found 5 days ago | See prices for these dates |
| 6 Nov – 9 Nov | $130 | Allegiant Air | Orlando Sanford International Airport (SFB) → Chicago Rockford International Airport (RFD) | out nonstop, back nonstop | found yesterday | See prices for these dates |
| 22 Nov – 23 Nov | $288 | Frontier Airlines | Orlando International Airport (MCO) → Chicago Midway International Airport (MDW) | out nonstop, back nonstop | found 2 days ago | See prices for these dates |
| 28 Nov – 1 Dec | $324 | Frontier Airlines | Orlando International Airport (MCO) → O'Hare International Airport (ORD) | out nonstop, back 1 stop | found today | See prices for these dates |
| 29 Nov – 1 Dec | $298 | Frontier Airlines | Orlando International Airport (MCO) → O'Hare International Airport (ORD) | out nonstop, back 1 stop | found today | See prices for these dates |
| 24 Apr 2027 – 26 Apr 2027 | $384 | American Airlines | Orlando International Airport (MCO) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| 29 Apr 2027 – 1 May 2027 | $384 | American Airlines | Orlando International Airport (MCO) → O'Hare International Airport (ORD) | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
Which month looks cheapest?
November 2026 is the cheapest month — from $130.
Airlines on the cheapest dates: Frontier Airlines, Allegiant Air, American Airlines.
One-way
The cheapest one-way fare on each of 6 departure dates is usually $65 to $125.
Cheapest one-way found recently
$67
2 Dec · Frontier Airlines
Orlando International Airport (MCO) → O'Hare International Airport (ORD)
Leaves 9:15 a.m. · 5 h 37 min trip
1 stop
found today
Cheapest nonstop one-way
$113
25 Nov · Allegiant Air
Orlando Sanford International Airport (SFB) → Chicago Rockford International Airport (RFD)
Leaves 6:15 a.m. · 2 h 51 min trip
nonstop
found 2 days ago
Found recently, and the cheapest we hold
$67 2 Decfound todayOpen this trip
$59 28 Octfound 6 days agoOpen this trip
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $51 to $124.
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 6 departure dates from 23 Oct to 2 Dec, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 2 Dec to compare.
Every date we hold
8 fares on 6 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 23 Oct | $129 | Allegiant Air | Orlando Sanford International Airport (SFB) → Chicago Rockford International Airport (RFD) | nonstop | found 5 days ago | Open this trip |
| 28 Oct | $59 | Allegiant Air | Orlando Sanford International Airport (SFB) → Chicago Rockford International Airport (RFD) | nonstop | found 6 days ago | Open this trip |
| 29 Oct | $143 | Allegiant Air | Orlando Sanford International Airport (SFB) → Chicago Midway International Airport (MDW) | 1 stop | found 6 days ago | Open this trip |
| 30 Oct | $64 | Allegiant Air | Orlando Sanford International Airport (SFB) → Chicago Rockford International Airport (RFD) | nonstop | found 5 days ago | Open this trip |
| 25 Nov | $113 | Allegiant Air | Orlando Sanford International Airport (SFB) → Chicago Rockford International Airport (RFD) | nonstop | found 2 days ago | Open this trip |
| 2 Dec | $67 | Frontier Airlines | Orlando International Airport (MCO) → O'Hare International Airport (ORD) | 1 stop | found today | Open this trip |
Which month looks cheapest?
October 2026 is the cheapest month — from $59.
Airlines on the cheapest dates: Allegiant Air, Frontier Airlines.
Premium cabin fares from Orlando to Chicago
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 6 Nov – 9 Nov in another cabin: Premium economy · Business · First
Today's prices for 2 Dec in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Orlando to Chicago?
Return
Fares 14 to 29 days before departure were typically 44% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 18 Oct (25 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $284 | $193 | +78% | 20 |
| 7–13 days | $211 | $132 | +32% | 24 |
| 14–29 days | $160 | $127 | Cheapest seen | 24 |
| 30–59 days | $178 | $119 | +11% | 18 |
| 60–89 days | $217 | $197 | +36% | 15 |
One-way
Fares 14 to 29 days before departure were typically 29% lower than 0 to 6 days before departure.
From the cheapest one-way each day between 24 Sept and 18 Oct (25 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $84 | $67 | +41% | 20 |
| 7–13 days | $67 | $59 | +13% | 22 |
| 14–29 days | $60 | $51 | Cheapest seen | 20 |
| 30–59 days | $69 | $56 | +16% | 12 |
| 60–89 days | $94 | $65 | +57% | 10 |
| 90–179 days | $85 | $62 | +42% | 24 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
Tampa → Chicago
124 km from Orlando
$255
$125 more than flying from Orlando
3 Nov – 5 Nov · TPA → MDW · out 1 stop, back 1 stop
found yesterday
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
One-way
Tampa → Chicago
124 km from Orlando
$101
$34 more than flying from Orlando
22 Dec · TPA → ORD · nonstop
found yesterday
Cheapest recent price on each route — one way, per traveler in Economy. Distances are in a straight line.
Live price for these dates
The cheapest return found recently is for 6 Nov – 9 Nov. A live search on this page shows what those dates cost now, for one adult in economy.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work