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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 Saturday

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

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

$229

Average for round-trip flights in January 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 18% on your trip compared to booking a flight in the afternoon.

Cheap flights from Madison to Chicago in January, February 2021

The best prices found for MSN to CHI flights for January, February
25 Feb - 3 Mar
$161pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
MSN
Madison Truax Field
25 Feb - 3 Mar
$168pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
MSN
Madison Truax Field
25 Feb - 3 Mar
$213pp
MSN
Madison Truax Field
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
MSN
Madison Truax Field

Madison to Chicago 2021 flight deals

Cheap flights to Chicago from Madison found for this year
25 Feb - 3 Mar
$161pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
MSN
Madison Truax Field
25 Feb - 3 Mar
$168pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
MSN
Madison Truax Field
25 Feb - 3 Mar
$213pp
MSN
Madison Truax Field
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
MSN
Madison Truax Field

Non-stop flights to Chicago from Madison

Save time with Madison to Chicago direct flight deals
4 Mar - 7 Mar
$307pp
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
12 Jul - 16 Jul
$455pp
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

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.

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.

Can I find flights from Madison to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Madison to Chicago for under $200. The cheapest flight booked recently is on Multiple Airlines for just $161, but on average you can expect to pay $341.

Are there nonstop flights from Madison to Chicago for under $400 on Cheapflights?

Cheapflights has at least 2 direct flights from Madison to Chicago under $400. A good price for a nonstop flight from Madison to Chicago is less than $381.

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 54m. This flight may include one or multiple stops.

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

Frontier, at $243, was found to be the cheapest airline from Madison to Chicago.Alternate airlines to your destination round-trip include American Airlines and United Airlines.

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
0h 56m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Madison

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Madison to Chicago

Morning 6 AM to noon 70% of MSN to CHI departures
Afternoon Noon to 6 PM 29% of MSN to CHI departures
Early morning Midnight to 6 AM 1% 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
15 daily flights
Monday
9 daily flights
Tuesday
5 daily flights
Wednesday
4 daily flights
Thursday
12 daily flights
Friday
15 daily flights
Saturday
9 daily flights
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