Cheap flights from Madison to Chicago (MSN - CHI)

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The best prices from Madison to Chicago are usually found in August or July, booked 29 days in advance, depart on a Saturday or Tuesday and return on a Wednesday

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

All the information you need to plan the best MSN to CHI flight in 2021: compare Madison to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
MSN - CHI
Price
$73 - $377
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

April

High demand for flights, 42% potential price rise

Cheapest in

August

Best time to find cheap flights, 67% potential price drop

Average price

$155

Average for round-trip flights in May 2021

Round-trip from

$73

From Madison to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
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 20 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 $137 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $157.

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

Our data shows that April tends to be the cheapest month to fly to Chicago from Madison. Users have commonly found prices around $135 for the month, but tickets can be as low as $33. Due to multiple factors, prepare for potentially higher prices in December.

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 26% on your trip compared to booking a flight in the afternoon.

Cheap flights from Madison to Chicago in May, June 2021

The best prices found for MSN to CHI flights for May, June
17 Jun - 19 Jun
$278pp
MSN
Madison Truax Field
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
MSN
Madison Truax Field
22 May - 3 Jun
$301pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
4 Jun - 6 Jun
$315pp
MSN
Madison Truax Field
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field

Madison to Chicago 2021 flight deals

Cheap flights to Chicago from Madison found for this year
15 Sep - 16 Sep
$268pp
MSN
Madison Truax Field
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
MSN
Madison Truax Field
17 Jun - 19 Jun
$278pp
MSN
Madison Truax Field
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
MSN
Madison Truax Field
14 Sep - 20 Sep
$298pp
MSN
Madison Truax Field
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
MSN
Madison Truax Field

Non-stop flights to Chicago from Madison

Save time with Madison to Chicago direct flight deals
17 Jun - 19 Jun
$278pp
MSN
Madison Truax Field
Major Airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Major Airline
Non-Stop
MSN
Madison Truax Field
22 May - 3 Jun
$301pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
9 Sep - 18 Sep
$327pp
MSN
Madison Truax Field
American 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
22 May - 3 Jun
$301pp
MSN
Madison Truax Field
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
MSN
Madison Truax Field
22 May - 26 May
$359pp
MSN
Madison Truax Field
Multiple Airlines
     
3 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field
22 May - 26 May
$367pp
MSN
Madison Truax Field
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field

One-way flights to Chicago from Madison

The cheapest one-way flights from Madison to Chicago
1:16 pm - 7:42 pm
Frontier
1 Stop
6h 26m
MSN - ORD
Frontier
$188
Kiwi.com
5:00 am - 10:54 am
United Airlines
1 Stop
5h 54m
MSN - ORD
United Airlines
$247
United
11:44 am - 7:58 pm
American Airlines
1 Stop
8h 14m
MSN - ORD
American Airlines

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Madison</span> to <span class="emphasized">Chicago</span> 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.

Which airlines flying from Madison Truax Field to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Madison Truax Field to Chicago have new flexible policies in place due to COVID-19. American Airlines, United Airlines, and Bus are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like American Airlines with this kind of flexibility.

What airport do you fly from for flights from Madison to Chicago?

For a flight from Madison to Chicago, you will be flying from Truax Field. Madison Truax Field (MSN) is just 5.4 mi from the center of the city. Truax Field is the only Madison airport and it handles 25 outbound flights to Chicago per day. 4 airlines have flights to Chicago from Madison Truax Field on a regular basis.

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 American Airlines for just $268, but on average you can expect to pay $328.

Are there nonstop flights from Madison to Chicago for under $300 on Cheapflights?

Cheapflights has at least 10 direct flights from Madison to Chicago under $300. A good price for a nonstop flight from Madison to Chicago is less than $395.

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

There are currently 20+ open flights from Madison to Chicago within the next 7 days for less than $400.

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 58m. All flights are typically nonstop.

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

American Airlines, at $268, was found to be the cheapest airline from Madison to Chicago.Alternate airlines to your destination round-trip include Major Airline and Delta.

What are the cheapest airlines to fly from Madison to Chicago one-way?

$188 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on United Airlines and American Airlines, with prices starting from $227 and $238, respectively.

Alternative routes for Madison to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Madison to Chicago.
Flight duration
1h 01m
Average temperature for May in Chicago
71.6 °F
Avg rainfall for May in Chicago
4.3 ″

Airports servicing Madison

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Madison to Chicago

See what time of day planes typically take off from Madison towards Chicago.
Morning 6 AM to noon 54% of MSN to CHI departures
Afternoon Noon to 6 PM 30% of MSN to CHI departures
Early morning Midnight to 6 AM 16% 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
See how many times per day planes take to the skies headed from Madison to Chicago.
Sunday
28 daily flights
Monday
26 daily flights
Tuesday
25 daily flights
Wednesday
26 daily flights
Thursday
24 daily flights
Friday
28 daily flights
Saturday
18 daily flights
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