Chicago to Orlando MDW, ORD, RFD → MCO, SFB
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Orlando International Airport (MCO), Orlando Sanford International Airport (SFB)
The cheapest return found recently is $185 with Frontier Airlines, 16 Nov – 25 Nov, found 17 hours ago. The cheapest one-way found recently is $75 with Frontier Airlines, 12 Jan 2027, found yesterday.
Return
The cheapest return fare on each of 12 departure dates is usually $196 to $305.
Cheapest return found recently
$185
16 Nov – 25 Nov · Frontier Airlines
Chicago Rockford International Airport (RFD) → Orlando Sanford International Airport (SFB)
Leaves 10:38 a.m. · Return leaves 8:47 a.m. · 12 h 50 min of travel, both ways together
out nonstop, back 1 stop · via Dallas/Fort Worth International Airport (DFW) · separate tickets likely: collect your bags and check in again · overnight connection
found 17 hours ago
Cheapest nonstop return
$208
16 Nov – 24 Nov · Frontier Airlines
Chicago Rockford International Airport (RFD) → Orlando Sanford International Airport (SFB)
Leaves 10:38 a.m. · Return leaves 8:47 p.m. · 5 h 37 min of travel, both ways together
out nonstop, back nonstop · separate tickets likely: collect your bags and check in again
found 17 hours ago
Every nonstop date from Chicago to Orlando
Found recently, and the cheapest we hold
$185 16 Nov – 25 Novfound 17 hours agoSee prices for these dates
$160 16 Nov – 24 Novfound 5 days agoSee prices for these dates
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $144 to $176.
At $185, the cheapest return found recently is above that range.
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 12 departure dates from 22 Oct to 18 Feb 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 9-night return fares leaving within 3 days of 16 Nov to compare.
Every date we hold
191 fares on 12 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 22 Oct – 23 Oct | $327 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | out 1 stop, back nonstop | found 4 days ago | See prices for these dates |
| 30 Oct – 2 Nov | $239 | Allegiant Air | Chicago Rockford International Airport (RFD) → Orlando Sanford International Airport (SFB) | out nonstop, back nonstop | found 3 days ago | See prices for these dates |
| 5 Nov – 9 Nov | $432 | Allegiant Air | Chicago Rockford International Airport (RFD) → Orlando International Airport (MCO) | out 1 stop, back nonstop | found 3 days ago | See prices for these dates |
| 7 Nov – 14 Nov | $179 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | out nonstop, back 1 stop | found 4 days ago | See prices for these dates |
| 12 Nov – 15 Nov | $255 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | out 1 stop, back nonstop | found 4 days ago | See prices for these dates |
| 14 Nov – 16 Nov | $161 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | out 1 stop, back 1 stop | found 6 days ago | See prices for these dates |
| 16 Nov – 24 Nov | $160 | Frontier Airlines | Chicago Rockford International Airport (RFD) → Orlando Sanford International Airport (SFB) | out nonstop, back 1 stop | found 5 days ago | See prices for these dates |
| 20 Nov – 27 Nov | $275 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | out 1 stop, back 1 stop | found 3 days ago | See prices for these dates |
| 11 Dec – 13 Dec | $202 | Frontier Airlines | Chicago Midway International Airport (MDW) → Orlando International Airport (MCO) | out 1 stop, back 1 stop | found 5 days ago | See prices for these dates |
| 25 Dec – 3 Jan 2027 | $962 | Allegiant Air | Chicago Rockford International Airport (RFD) → Orlando International Airport (MCO) | out 2 stops, back 2 stops | found yesterday | See prices for these dates |
| 10 Feb 2027 – 14 Feb 2027 | $293 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | out 1 stop, back nonstop | found 3 days ago | See prices for these dates |
| 18 Feb 2027 – 21 Feb 2027 | $297 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | out nonstop, back nonstop | found 2 days ago | See prices for these dates |
Which month looks cheapest?
November 2026 is the cheapest month — from $160.
Airlines on the cheapest dates: Frontier Airlines, Allegiant Air.
One-way
The cheapest one-way fare on each of 9 departure dates is usually $102 to $135.
Cheapest one-way found recently
$75
12 Jan 2027 · Frontier Airlines
O'Hare International Airport (ORD) → Orlando International Airport (MCO)
Leaves 6:00 a.m. · 7 h 43 min trip
1 stop · via Hartsfield-Jackson Atlanta International Airport (ATL)
found yesterday
Cheapest nonstop one-way
$135
12 Jan 2027 · Frontier Airlines
O'Hare International Airport (ORD) → Orlando International Airport (MCO)
Leaves 5:01 a.m. · 2 h 54 min trip
nonstop
found yesterday
Every nonstop date from Chicago to Orlando
Found recently, and the cheapest we hold
$75 12 Jan 2027found yesterdayOpen this trip
It is also the cheapest one-way we hold, of any age.
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $62 to $100.
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 9 departure dates from 23 Oct to 12 Jan 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 one-way fares leaving within 3 days of 12 Jan 2027 to compare.
Every date we hold
87 fares on 9 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 23 Oct | $135 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | nonstop | found 6 days ago | Open this trip |
| 30 Oct | $126 | Allegiant Air | Chicago Rockford International Airport (RFD) → Orlando Sanford International Airport (SFB) | nonstop | found 3 days ago | Open this trip |
| 5 Nov | $128 | Allegiant Air | Chicago Rockford International Airport (RFD) → Orlando International Airport (MCO) | 1 stop | found 5 days ago | Open this trip |
| 7 Nov | $102 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | 1 stop | found yesterday | Open this trip |
| 20 Nov | $256 | Allegiant Air | Chicago Rockford International Airport (RFD) → Orlando Sanford International Airport (SFB) | nonstop | found 3 days ago | Open this trip |
| 24 Nov | $240 | Allegiant Air | Chicago Rockford International Airport (RFD) → Orlando International Airport (MCO) | 1 stop | found yesterday | Open this trip |
| 1 Dec | $75 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | 1 stop | found 4 days ago | Open this trip |
| 22 Dec | $128 | Southwest Airlines | Chicago Midway International Airport (MDW) → Orlando International Airport (MCO) | 1 stop | found 4 hours ago | Open this trip |
| 12 Jan 2027 | $75 | Frontier Airlines | O'Hare International Airport (ORD) → Orlando International Airport (MCO) | 1 stop | found yesterday | Open this trip |
Which month looks cheapest?
December 2026 is the cheapest month — from $75.
Airlines on the cheapest dates: Frontier Airlines, Allegiant Air, Southwest Airlines.
Premium cabin fares from Chicago to Orlando
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 16 Nov – 25 Nov in another cabin: Premium economy · Business · First
Today's prices for 12 Jan 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Orlando?
Return
Fares 14 to 29 days before departure were typically 37% 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 | $254 | $147 | +58% | 17 |
| 7–13 days | $285 | $144 | +77% | 10 |
| 14–29 days | $161 | $144 | Cheapest seen | 25 |
| 30–59 days | $176 | $144 | +9% | 25 |
| 60–89 days | $230 | $198 | +43% | 25 |
| 90–179 days | $227 | $181 | +41% | 24 |
One-way
Fares 90 to 179 days before departure were typically 46% 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 | $154 | $120 | +84% | 19 |
| 7–13 days | $154 | $126 | +84% | 19 |
| 14–29 days | $147 | $68 | +76% | 21 |
| 30–59 days | $88 | $75 | +5% | 8 |
| 60–89 days | $97 | $65 | +16% | 23 |
| 90–179 days | $84 | $62 | Cheapest seen | 24 |
| 180+ days | $101 | $101 | +21% | 10 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
Chicago → Tampa
124 km from Orlando
$193
$8 more than flying to Orlando
19 Dec – 29 Dec · ORD → TPA · out nonstop, back nonstop
found yesterday
Milwaukee → Orlando
131 km from Chicago
$414
$229 more than flying from Chicago
12 Mar 2027 – 20 Mar 2027 · MKE → MCO · out 1 stop, back nonstop
found 2 days ago
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
One-way
Milwaukee → Orlando
131 km from Chicago
$63
$12 less than flying from Chicago
23 Nov · MKE → MCO · nonstop
found 6 days ago
Chicago → Tampa
124 km from Orlando
$99
$24 more than flying to Orlando
5 Nov · RFD → TPA · 1 stop
found 2 days ago
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 16 Nov – 25 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