Menu

Cheap flights from Madison to Chicago (MSN - CHI)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

How to find the cheapest flight from
Madison (MSN) to Chicago (CHI)

What is the cheapest day to fly round-trip from Madison to Chicago?

Saturday flights are found to be more expensive to fly from Madison to Chicago. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

How far in advance should I book a flight from Madison to Chicago?

To save on the cost of your flight from Madison to Chicago, book at least 37 days before your planned departure. Booking around this time can save you about 10% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $177 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $177.

When is the cheapest time to fly from Madison to Chicago (MSN - CHI)?

A simple way to save on the total cost of your ticket is to fly from Madison to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 18% on your trip compared to booking a flight in the afternoon.

Cheap flights from Madison to Chicago in September, October 2020

The best prices found for MSN to CHI flights for September, October
24 Oct - 26 Oct
$304pp
MSN
Madison Truax Field
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
MSN
Madison Truax Field
4 Oct - 6 Oct
$306pp
MSN
Madison Truax Field
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
MSN
Madison Truax Field
4 Oct - 6 Oct
$579pp
MSN
Madison Truax Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
MSN
Madison Truax Field

Madison to Chicago 2020 flight deals

Cheap flights to Chicago from Madison found for this year
15 Nov - 17 Nov
$264pp
MSN
Madison Truax Field
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
MSN
Madison Truax Field
24 Oct - 26 Oct
$304pp
MSN
Madison Truax Field
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
MSN
Madison Truax Field
12 Nov - 15 Nov
$304pp
MSN
Madison Truax Field
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
MSN
Madison Truax Field

Non-stop flights to Chicago from Madison

Save time with Madison to Chicago direct flight deals
21 Nov - 29 Nov
$491pp
MSN
Madison Truax Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
15 Jan - 18 Jan
$585pp
MSN
Madison Truax Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
MSN
Madison Truax Field

Last minute flights from Madison to Chicago

Late deals on round-trip flights to Chicago from Madison, departing today and this week
4 Oct - 6 Oct
$306pp
MSN
Madison Truax Field
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
MSN
Madison Truax Field
4 Oct - 6 Oct
$579pp
MSN
Madison Truax Field
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
MSN
Madison Truax Field

One-way flights to Chicago from Madison

The cheapest one-way flights from Madison to Chicago
2:00 am - 12:46 pm
Multiple Airlines
2 Stops
10h 46m
MSN - ORD
Multiple Airlines
$941
Kiwi.com
2:26 pm - 3:12 pm
Multiple Airlines
2 Stops
24h 46m
MSN - MDW
Multiple Airlines
$2,682
Kiwi.com

Related info for your journey

Useful info, stats and facts about Madison to Chicago flights.

Flight FAQs

From Madison to Chicago

Are flight prices decreasing from Madison to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Madison and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Madison to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Madison to Chicago for under $300. The cheapest flight booked recently is on Delta for just $264, but on average you can expect to pay $701.

Are there nonstop flights from Madison to Chicago for under $500 on Cheapflights?

Cheapflights has at least 2 direct flights from Madison to Chicago under $500. A good price for a nonstop flight from Madison to Chicago is less than $538.

Are there last-minute flights available from Madison to Chicago for under $400?

There are currently 2+ open flights from Madison to Chicago within the next 7 days for less than $400.

What days are nonstop flights available from Madison to Chicago?

Nonstop flights can be found on the following days: Sunday, Monday, Tuesday, Thursday, Saturday.

How many flights depart from Madison to Chicago on average per day?

Travelers can expect 8 flights from Madison Truax Field to Chicago on average per day.
Morning (6am - Noon) - 100% of flight departures

Is Madison weather warmer or cooler than Chicago?

You can imagine temperatures to be in the 84 °F range in July. The weather in Chicago is generally the same as Madison's. As flight availability is subject to become more limited as peak season approaches it is ideal to book in a timely manner.

How long is the flight from Madison to Chicago?

Departing from Madison to Chicago will take you 4h 45m. There are 109 mi between Madison and Chicago. This flight may include one or multiple stops.

What are the cheapest airlines flying from Madison to Chicago round-trip?

Delta, at $264, was found to be the cheapest airline from Madison to Chicago. An alternate airline flying to your destination would be Linear Air Taxi. Delta is currently priced 8% below the average price you’ll pay for this route.

Alternative routes for Madison to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Madison to Chicago
Flight duration
1h 01m
Average temperature for September in Chicago
77.0 °F
Avg rainfall for September in Chicago
2.4 ″

Airports servicing Madison

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Madison to Chicago

Morning 6 AM to noon 61% of MSN to CHI departures
Early morning Midnight to 6 AM 25% of MSN to CHI departures
Afternoon Noon to 6 PM 14% of MSN to CHI departures
Evening 6 PM to midnight 0% of MSN to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Madison to Chicago
Sunday
26 daily flights
Monday
22 daily flights
Tuesday
26 daily flights
Wednesday
25 daily flights
Thursday
25 daily flights
Friday
28 daily flights
Saturday
24 daily flights
Home North America USA Illinois Chicago Cheap flights from Madison to Chicago