MSN - CHI

$140 Find Cheap Flights from Madison to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Chicago departing on 1/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$179
United Airlines
Thu 1/22Sun 1/25
MSN - ORD • Non-stop
Cheapest one-way
$140
Typical prices: $124-$194
Multiple Airlines
Fri 1/16
MSN - ORD • 1 stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Basic Economy is budget-friendly with carry-on.
United's Priority Boarding secures overhead bin space.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
United Airlines
Cheapest • from $179 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MSN-ORD
Cheapest
MSN-ORD
Most popular
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Madison to Chicago (MSN-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Chicago

Thu, Jan 22 - Sun, Jan 25
United Airlines Logo
12:32 pm - 1:53 pm
MSN
-
ORD
1h 21mnonstop
United Airlines Logo
8:00 pm - 9:05 pm
ORD
-
MSN
1h 05mnonstop
$179United Airlines
Wed, Jun 3 - Mon, Jun 8
United Airlines Logo
6:45 am - 7:50 am
MSN
-
ORD
1h 05mnonstop
United Airlines Logo
7:50 pm - 8:54 pm
ORD
-
MSN
1h 04mnonstop
$190United Airlines
Thu, May 21 - Sat, May 30
United Airlines Logo
6:45 am - 7:50 am
MSN
-
ORD
1h 05mnonstop
United Airlines Logo
8:55 am - 9:53 am
ORD
-
MSN
0h 58mnonstop
$192United Airlines
Thu, Jan 1 - Sun, Jan 4
American Airlines Logo
6:00 am - 7:14 am
MSN
-
ORD
1h 14mnonstop
American Airlines Logo
4:38 pm - 5:47 pm
ORD
-
MSN
1h 09mnonstop
$209American Airlines
Thu, Mar 12 - Thu, Mar 19
United Airlines Logo
3:54 pm - 5:05 pm
MSN
-
ORD
1h 11mnonstop
United Airlines Logo
1:57 pm - 2:58 pm
ORD
-
MSN
1h 01mnonstop
$212United Airlines
Tue, Feb 24 - Sun, Mar 8
American Airlines Logo
9:43 am - 10:54 am
MSN
-
ORD
1h 11mnonstop
American Airlines Logo
8:06 am - 9:14 am
ORD
-
MSN
1h 08mnonstop
$223American Airlines
Fri, Dec 26 - Tue, Dec 30
American Airlines Logo
8:10 pm - 9:30 pm
MSN
-
ORD
1h 20mnonstop
American Airlines Logo
4:38 pm - 5:47 pm
ORD
-
MSN
1h 09mnonstop
$224American Airlines
Wed, Jan 7 - Sun, Jan 18
Multiple Airlines Logo
6:16 pm - 11:31 am
MSN
-
MDW
17h 15m2 stops
Multiple Airlines Logo
8:19 pm - 1:48 pm
MDW
-
MSN
17h 29m1 stop
$362Multiple Airlines
Fri, Dec 26 - Tue, Dec 30
Multiple Airlines Logo
2:53 pm - 3:28 pm
MSN
-
MDW
24h 35m2 stops
Multiple Airlines Logo
3:10 pm - 5:28 pm
MDW
-
MSN
26h 18m1 stop
$711Multiple Airlines
Fri, Dec 26 - Tue, Dec 30
Frontier Logo
2:53 pm - 9:19 am
MSN
-
MDW
18h 26m2 stops
Frontier Logo
2:01 pm - 2:15 pm
MDW
-
MSN
24h 14m1 stop
$811Frontier
Booking Insights

KAYAK's insights & trends for Madison to Chicago flights

Get data-powered insights and trends into flights from Madison to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Madison to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Madison to Chicago costs $248 on the route between Madison (MSN) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Madison to Chicago?

The average price of all round-trip flights from Madison to Chicago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Madison to Chicago, look for departures on Fridays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago, Friday is the cheapest day to fly and Monday is the most expensive.

Expert advice

Expert advice for your flight from Madison to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Basic Economy for budget travel with carry-on only, but compare total costs with Main Cabin.


Main Cabin Extra offers early boarding and complimentary drinks, ideal for a quick, comfortable journey.

United Airlines

United First offers ample legroom, up to 7 inches more than economy, enhancing comfort on short flights.


Purchase Priority Boarding to ensure overhead bin space, placing you in Zone 2 for quicker boarding.

Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more

Good to know

Low seasonJune
Cheapest flight$140
Best time to beat the crowds with an average 25% drop in price.
Flight from Madison to Chicago O'Hare Airport

When to book flights from Madison to Chicago

Are your dates flexible? Find out the best times to travel from Madison to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Madison to Chicago

  • What is the cheapest flight from Madison to Chicago?

    In the last 3 days, the lowest price for a flight from Madison to Chicago was $140 for a one-way ticket and $179 for a round-trip.

  • Do I need a passport to fly between Madison and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airlines offer Wi-Fi service onboard planes from Madison to Chicago?

    American Airlines, Delta, and Japan Airlines offer inflight Wi-Fi service on the Madison to Chicago flight route.

  • Which aircraft models fly most regularly from Madison to Chicago?

    The Embraer 175 is the aircraft model that flies most regularly on the Madison to Chicago flight route.

  • Which airline alliances offer flights from Madison to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Madison and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Madison to Chicago?

    There are nonstop flights from Madison to Chicago on a daily basis.

  • How does KAYAK find such low prices on flights from Madison to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Madison is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Madison with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Madison to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $238 or less one-way and $320 or less round-trip.

Prefer to fly direct from Madison to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Madison Truax Field to Chicago.
Find which airlines fly direct from Madison Truax Field Airport to Chicago, which days they fly and book direct flights.

Direct departures

Madison Truax Field to Chicago

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Direct returns

Chicago to Madison Truax Field

Monday

American Airlines, United Airlines

American Airlines, United Airlines

Tuesday

American Airlines, United Airlines

American Airlines, United Airlines

Wednesday

American Airlines, United Airlines

American Airlines, United Airlines

Thursday

American Airlines, United Airlines

American Airlines, United Airlines

Friday

American Airlines, United Airlines

American Airlines, United Airlines

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

Sunday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights

Reviews of the top airline flying from Madison to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Madison to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Madison to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9095 reviews
6.6Food
7.7Boarding
7.1Entertainment
8.1Crew
7.3Comfort
Airline reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

10.0 ExcellentRoger, Dec 2025
CAE - ORD
Read more United Airlines reviews

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Everything you need to know for your flight from Madison to Chicago

Information on your arrival and departure airports