Madison to Chicago MSN → ORD
Dane County Regional Airport (MSN) → O'Hare International Airport (ORD)
The cheapest one-way found recently is $261 with American Airlines, 21 Dec, found 2 days ago.
One-way
The cheapest one-way fare on each of 3 departure dates is usually $229 to $251.
Cheapest one-way found recently
$261
21 Dec · American Airlines
Dane County Regional Airport (MSN) → O'Hare International Airport (ORD)
Leaves 5:00 a.m. · 1 h 21 min trip
nonstop
found 2 days ago
Cheapest nonstop one-way
$261
21 Dec · American Airlines
Dane County Regional Airport (MSN) → O'Hare International Airport (ORD)
Leaves 5:00 a.m. · 1 h 21 min trip
nonstop
found 2 days ago
Found recently, and the cheapest we hold
$261 21 Decfound 2 days agoOpen this trip
$218 23 Octfound 6 days agoOpen this trip
What have prices looked like?
Over 18 days, 26 Sept to 18 Oct, the cheapest one-way we saw each day was $208 to $325.
18 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 3 departure dates from 23 Oct to 21 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 21 Dec to compare.
Every date we hold
3 fares on 3 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 23 Oct | $218 | United Airlines | Dane County Regional Airport (MSN) → O'Hare International Airport (ORD) | nonstop | found 6 days ago | Open this trip |
| 26 Oct | $240 | United Airlines | Dane County Regional Airport (MSN) → O'Hare International Airport (ORD) | nonstop | found 3 days ago | Open this trip |
| 21 Dec | $261 | American Airlines | Dane County Regional Airport (MSN) → O'Hare International Airport (ORD) | nonstop | found 2 days ago | Open this trip |
Which month looks cheapest?
October 2026 is the cheapest month — from $218.
Airlines on the cheapest dates: United Airlines, American Airlines.
Premium cabin fares from Madison 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 21 Dec in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Madison to Chicago?
One-way
Fares 7 to 13 days before departure were typically 20% lower than 0 to 6 days before departure.
From the cheapest one-way each day between 26 Sept and 18 Oct (18 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 | $272 | $208 | +25% | 12 |
| 7–13 days | $218 | $208 | Cheapest seen | 12 |
| 14–29 days | $249 | $249 | +14% | 8 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
One-way
Milwaukee → Chicago
122 km from Madison
$175
$86 less than flying from Madison
31 Oct · MKE → ORD · nonstop
found 3 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 one-way found recently is for 21 Dec. 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