ORD - MSN

$173 Find Cheap Flights from Chicago O'Hare Airport to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to Madison departing on 5/26. 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 Madison

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

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Everything you should know

Cheapest round-trip
$239
United Airlines
Fri 4/17Mon 4/20
ORD - MSN • Non-stop
Cheapest one-way
$173
Typical prices: $213-$352
Multiple Airlines
Tue 5/26
ORD - MSN • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
American's Basic Economy has low fares but restrictions.
United's Priority Boarding in Zone 2 secures bin space.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $239 (round-trip)
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines and United Airlines. Average duration is 1h 06m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Most punctual • 82% on-time
Best time • Fewest delays
Insights
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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 Madison!
Flight Deals
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Flight Deals

Cheap Flights from O'Hare Intl to Madison (ORD-MSN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to Madison 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 O'Hare Intl to Madison

Fri, Apr 17 - Mon, Apr 20
United Airlines Logo
7:45 am - 8:57 am
ORD
-
MSN
1h 12mnonstop
United Airlines Logo
8:35 pm - 9:37 pm
MSN
-
ORD
1h 02mnonstop
$239United Airlines
Fri, May 8 - Fri, May 15
American Airlines Logo
10:35 pm - 11:41 pm
ORD
-
MSN
1h 06mnonstop
American Airlines Logo
2:18 pm - 3:38 pm
MSN
-
ORD
1h 20mnonstop
$240American Airlines
Thu, Apr 16 - Sun, Apr 19
American Airlines Logo
8:40 am - 9:48 am
ORD
-
MSN
1h 08mnonstop
American Airlines Logo
3:01 pm - 4:16 pm
MSN
-
ORD
1h 15mnonstop
$241American Airlines
Sun, Jun 7 - Sat, Jun 27
American Airlines Logo
6:40 am - 7:49 am
ORD
-
MSN
1h 09mnonstop
American Airlines Logo
11:25 am - 12:42 pm
MSN
-
ORD
1h 17mnonstop
$261American Airlines
Thu, May 7 - Thu, May 14
American Airlines Logo
1:24 pm - 2:33 pm
ORD
-
MSN
1h 09mnonstop
American Airlines Logo
2:18 pm - 3:38 pm
MSN
-
ORD
1h 20mnonstop
$268American Airlines
Wed, Apr 8 - Sun, Apr 12
American Airlines Logo
1:24 pm - 2:31 pm
ORD
-
MSN
1h 07mnonstop
American Airlines Logo
2:18 pm - 3:38 pm
MSN
-
ORD
1h 20mnonstop
$269American Airlines
Sat, Apr 4 - Wed, Apr 8
American Airlines Logo
6:50 pm - 7:52 pm
ORD
-
MSN
1h 02mnonstop
American Airlines Logo
5:37 pm - 7:05 pm
MSN
-
ORD
1h 28mnonstop
$284American Airlines
Sat, May 9 - Sat, May 16
Multiple Airlines Logo
9:42 pm - 8:25 am
ORD
-
MSN
34h 43m
2 stops
Multiple Airlines Logo
9:54 am - 9:27 am
MSN
-
ORD
23h 33m
1 stop
$288Multiple Airlines
Tue, May 5 - Sat, May 9
United Airlines Logo
7:45 am - 8:56 am
ORD
-
MSN
1h 11mnonstop
United Airlines Logo
2:25 pm - 3:36 pm
MSN
-
ORD
1h 11mnonstop
$309United Airlines
Thu, Apr 16 - Sun, Apr 19
American Airlines Logo
5:00 am - 10:55 am
ORD
-
MSN
5h 55m
1 stop
American Airlines Logo
8:24 pm - 9:40 pm
MSN
-
ORD
1h 16mnonstop
$320American Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Madison flights

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

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Madison?

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

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

Expert advice

Expert advice for your flight from O'Hare Intl to Madison

 
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.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

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.

Good to know

Cheapest flight$173
Flight from Chicago O'Hare Airport to Madison

When to book flights from O'Hare Intl to Madison

Are your dates flexible? Find out the best times to travel from O'Hare Intl to Madison 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 Chicago O'Hare Airport to Madison flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Madison?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Madison was $173 for a one-way ticket and $239 for a round-trip.

  • Do I need a passport to fly between Chicago O'Hare Airport and Madison?

    A passport is not required to fly from Chicago O'Hare Airport to Madison.

  • Which airlines offer Wi-Fi service onboard planes from Chicago O'Hare Airport to Madison?

    Only American Airlines offers inflight Wi-Fi service on the Chicago O'Hare Airport to Madison flight route.

  • Which aircraft models fly most regularly from Chicago O'Hare Airport to Madison?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Chicago O'Hare Airport to Madison flight route.

  • Which airline alliances offer flights from Chicago O'Hare Airport to Madison?

    Star Alliance is the only airline alliance operating flights between Chicago O'Hare Airport and Madison.

  • On which days can I fly direct from Chicago O'Hare Airport to Madison?

    There are nonstop flights from Chicago O'Hare Airport to Madison on a daily basis.

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Madison?

    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 Chicago O'Hare Airport to Madison.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from Chicago O'Hare Airport 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 Chicago O'Hare Airport to Madison?

    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 Madison with an airline and back to Chicago O'Hare Airport with another airline. Booking your flights between Chicago O'Hare Airport and MSN can sometimes prove cheaper using this method.

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

    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 Madison from Chicago O'Hare Airport 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 Chicago O'Hare Intl Airport to Madison

  • Looking for a cheap flight? 25% of our users found flights on this route for $234 or less one-way and $431 or less round-trip.

Prefer to fly direct from Chicago O'Hare Airport to Madison?

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

Direct departures

Chicago O'Hare Intl 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

Direct returns

Madison Truax Field to Chicago O'Hare Intl

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 O'Hare Intl to Madison

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Madison. 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 O'Hare Intl to Madison? 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 9483 reviews
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
6.6Food
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Everything you need to know for your flight from O'Hare Intl to Madison

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