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Cheap flights from Madison to Chicago (MSN - CHI)

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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.

Cheap flights from Madison to Chicago in July, August 2020

The best prices found for MSN to CHI flights for July, August
10 Jul - 14 Jul
$235pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field
10 Jul - 13 Jul
$261pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field
2 Jul - 5 Jul
$262pp
MSN
Madison Truax Field
Allegiant Air
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Allegiant Air
Non-Stop
MSN
Madison Truax Field

Madison to Chicago 2020 flight deals

Cheap flights to Chicago from Madison found for this year
10 Jul - 14 Jul
$235pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field
10 Jul - 13 Jul
$261pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field
2 Jul - 5 Jul
$262pp
MSN
Madison Truax Field
Allegiant Air
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Allegiant Air
Non-Stop
MSN
Madison Truax Field

Non-stop flights to Chicago from Madison

Save time with Madison to Chicago direct flight deals
2 Jul - 5 Jul
$262pp
MSN
Madison Truax Field
Allegiant Air
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Allegiant Air
Non-Stop
MSN
Madison Truax Field
10 Jul - 14 Jul
$277pp
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
2 Jul - 5 Jul
$337pp
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

Last minute flights from Madison to Chicago

Late deals on round-trip flights to Chicago from Madison, departing today and this week
26 Jun - 28 Jun
$289pp
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
25 Jun - 28 Jun
$365pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
MSN
Madison Truax Field
25 Jun - 29 Jun
$424pp
MSN
Madison Truax Field
Multiple Airlines
   
2 STOPS
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
2:30 am - 4:59 pm
Multiple Airlines
2 Stops
38h 29m
MSN - ORD
Multiple Airlines
$275
Kiwi.com
2:30 am - 12:21 pm
Sun Country Air
2 Stops
9h 51m
MSN - ORD
Sun Country Air
$321
Kiwi.com
4:51 am - 5:44 am
Linear Air Taxi
Nonstop
0h 53m
MSN - ORD
Linear Air Taxi
$1404
KAYAK

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 Multiple Airlines for just $235, but on average you can expect to pay $485.

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

Cheapflights has at least 9 direct flights from Madison to Chicago under $300. A good price for a nonstop flight from Madison to Chicago is less than $1448.

Are there last-minute flights available from Madison to Chicago for under $300?

There are currently 10+ open flights from Madison to Chicago within the next 7 days for less than $300.

What days are nonstop flights available from Madison to Chicago?

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

What is the cheapest airline for this route?

When searching, try setting your filters to view flights for ExpressJet, as currently they have the cheapest options available from Madison to Chicago. On average you can find 112 flights for this flight path daily.

How long does the flight from Madison to Chicago take?

Travelers can expect a nonstop flight to take approximately 1 hour, flying a distance of about 68 miles.

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

Travelers can expect 4 flights from Madison Truax Field to Chicago on average per day.
Morning (6am - Noon) - 25% of flight departures
Afternoon (Noon - 6pm) - 75% 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.

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 59m
Average temperature for July in Chicago
84.2 °F
Avg rainfall for July in Chicago
3.7 ″

Airports servicing Madison

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Madison to Chicago

Afternoon Noon to 6 PM 61% of MSN to CHI departures
Morning 6 AM to noon 38% 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
11 daily flights
Monday
11 daily flights
Tuesday
11 daily flights
Wednesday
9 daily flights
Thursday
11 daily flights
Friday
11 daily flights
Saturday
9 daily flights