Madison, WI MSN to Chicago, IL CHI flight with Republic Airlines

Sat, Feb 28
+ Add return
Republic Airlines
Ryanair
Vueling Airlines
KM Malta Airlines
easyJet
1,000+ travel companies
Republic Airlines
Ryanair
Vueling Airlines
KM Malta Airlines
easyJet
1,000+ travel companies
QR-Code
Scan to get our free app
Use our app to get live travel updates and book mobile tickets for trains, buses, flights, and ferries.
App Store
rate4.9
42K ratings
Google Play
rate4.6
136K reviews

Journey information

Overview: Madison, WI to Chicago, IL flight

USAUSA
USAUSA
Icon of flight

Flights from Madison, WI to Chicago, IL depart on average 19 times per day, taking around 1h 11m. Cheap flight tickets for this journey start at $223 (€177) but you can travel from only $27 (€21) by bus.

There are 8 flights per day. The earliest flight runs at 00:02, the last at 23:55. The fastest flight covers the 123 miles (198 km) distance in 1h 7m. February is the cheapest month to fly.

Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $27 (€21)
Distance
123 miles (198 km)
Average flight duration
1h 11m
Cheapest ticket price
$223 (€177)
Flights per day
19
Direct flights
8
Fastest flight
1h 7m
Cheapest month
February
First flight
00:02
Last flight
23:55
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Bus from $27 (€21)

The cheapest and fastest flights from Madison, WI to Chicago, IL

Showing times and prices for Mar 02

Cheapest price

$355

Average price

$359

Fastest journey

1 h 9 m

Average duration

1 h 13 m

Flights per day

5

Distance

198 km

Cheap tickets

The best way to find a cheap flight ticket from Madison, WI to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.

The average ticket from Madison, WI to Chicago, IL will cost around $359 if you buy it on the day, but the cheapest tickets can be found for only $355.

Fast flights

Of the 5 flights that leave Madison, WI for Chicago, IL onMon, Mar 02, 5 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.

On Mon, Mar 02 the direct flights cover the 198 km distance in an average of 1 h 13 m but if you time it right, some flights will get you there in just 1 h 9 m .

On Mon, Mar 02 the longest flights will take 1 h 17 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

United
11:25PM1h20
Madison, WI
12:45AMChicago, IL
$3551One-way
0 transfers
United
06:32PM1h21
Madison, WI
07:53PMChicago, IL
$3561One-way
0 transfers
United
11:38PM1h09
Madison, WI
12:47AMChicago, IL
$3581One-way
0 transfers
American Airlines
11:00AM1h15
Madison, WI
12:15PMChicago, IL
$3611One-way
0 transfers
United
09:48PM1h17
Madison, WI
11:05PMChicago, IL
$3641One-way
0 transfers

Travel Information

Compare bus and flight for Madison, WI to Chicago, IL

Omio recommends booking the bus as it is the most popular option from Madison, WI to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $27. For those with little time consider booking a flight which can get you there in 1h 11m. The ticket price range depends on the travel mode: a bus costs an average of $27, and a flight costs an average of $223.

Distance: 123 miles (198 km)

Compare flight with

Flight
Most popular
Bus

$342

Average price

$40

Average price

Cheapest

4h 11m

Average total duration

Fastest

1h 11m

Onboard

+

3h 0m

Additional time*

3h 56m

Average total duration

3h 26m

Onboard

+

30m

Additional time*

Republic Airlines

Most popular airline

FlixBus

Most popular bus company

Direct Options

Direct Options

Live departures

Madison, WI to Chicago, IL flight times

The table below shows live departures for Madison, WI to Chicago, IL flights for today, Sunday, March 1. You can also manually refresh the results below to see updated flight journeys.

Last updated at 11:38 PM
ProviderDepartsDurationArrivesTransfers
Tickets
unitedUA450211:44 PM Dane County Regional Airport
1h11
12:55 AM O'Hare International Airport0 transfersDirect
Monday, March 2
envoy_airAA39532:24 AM Dane County Regional Airport
1h07
3:31 AM O'Hare International Airport0 transfersDirect
american_airlines11:00 AM Madison, WI
1h15
12:15 PM Chicago, IL0 transfersDirect
american_airlines11:45 AM Madison, WI
1h14
12:59 PM Chicago, IL0 transfersDirect
united12:30 PM Madison, WI
1h11
1:41 PM Chicago, IL0 transfersDirect
united11:26 PM Madison, WI
1h21
12:47 AM Chicago, IL0 transfersDirect
united11:38 PM Madison, WI
1h09
12:47 AM Chicago, IL0 transfersDirect

This is the last flight of the day.

Find all the dates and times for this journey

How far in advance should I book flight tickets from Madison, WI to Chicago, IL?

The best time to book your flight from Madison, WI to Chicago, IL is 63 days before departure. See how prices for flights change on the Madison, WI to Chicago, IL route.
Prices are for one-way tickets for one passenger from Madison, WI to Chicago, IL per month. Insights are sourced from fares found by Omio users in the last 12 months. Current prices may differ as prices vary depending on the time of day, class or how far in advance you book your flight from Madison, WI to Chicago, IL.

Compare prices and tickets Madison, WI to Chicago, IL by bus or flight

Compare bus and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.

Mon
Mar 02
Tue
Mar 03
Wed
Mar 04
Thu
Mar 05
Fri
Mar 06
Sat
Mar 07
Sun
Mar 08

Airlines: Republic Airlines from Madison, WI to Chicago, ILFind the best flights between Madison, WI to Chicago, IL with Omio's travel partners Republic Airlines from $27 (€21). We can find you the best deals, schedules and tickets when comparing and booking the best trip.

Republic Airlines

About
Republic Airways is a major regional airline in the United States, operating as a subsidiary of Republic Airways Holdings. It provides scheduled passenger service for American Airlines (as American Eagle), Delta Air Lines (as Delta Connection), and United Airlines (as United Express) using a fleet of Embraer 170 and 175 regional jets. Headquartered in Indianapolis, Indiana, Republic Airways operates over 900 daily flights to more than 80 cities across the U.S. and Canada. The company is known for its large fleet of Embraer E-Jets and its state-of-the-art training facilities. In April 2025, Republic Airways Holdings announced its acquisition of Mesa Air Group, which is expected to create the second-largest regional carrier in the U.S.
Luggage & cancellation policy
Average Duration
1h 12m
Cheapest Price
$275 (€219)
Republic Airlines frequency
1 a day
Luggage included
One carry-on bag (24 x 16 x 10) and one personal item
Additional luggage
Checked bags for a fee
Cancellation Policy
Tickets are non-refundable but may be cancelled for future flight credit minus applicable fees
Pregnant on board
Passengers can fly up to the end of their 36th week for single pregnancies and the end of their 32nd week for multiple pregnancies
Unaccompagned minor
Unaccompanied minor service is available for children ages 5-14. Must be booked directly with Republic Airlines
Amenities on board the airplane
USB plugs
Accessibility
Republic Airlines offers assistance for passengers with reduced mobility, including wheelchair services and priority boarding. Passengers are advised to request these services in advance to ensure availability and proper arrangements.

FAQs: Madison, WI to Chicago, IL Flight

Find answers to the most common questions about traveling from Madison, WI to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

FAQs
Cheap plane tickets from Madison, WI to Chicago, IL can start from as little as $223 (€177) when you book in advance. The average flight ticket price for Madison, WI to Chicago, IL is $342 (€272) ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by plane from Madison, WI to Chicago, IL is 1h 7m to travel the 123 miles (198 km) long route. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
The earliest flight from Madison, WI to Chicago, IL leaves at 12:02 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Madison, WI to Chicago, IL leaves at 11:55 PM.
Yes, there are 8 direct flights a day from Madison, WI to Chicago, IL with Republic Airlines. Schedules can vary on holidays or weekends with fewer direct flights.
When taking a flight from Madison, WI to Chicago, IL, you can count on Republic Airlines for the best way to get you to Chicago, IL. You can also check all possible airlines who offer a service between Madison, WI and Chicago, IL and compare the amenities they offer before buying a plane ticket.
The cheapest month for a flight from Madison, WI to Chicago, IL is February.
It's helpful to compare your options as there are 2 ways to travel between Madison, WI and Chicago, IL including taking a bus and flight.
Since neither Madison, WI nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
There is no time difference between Madison, WI and Chicago, IL.
The best events to attend in Chicago, IL include:
  • Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan
  • Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park
  • Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.
The best holidays to experience in Chicago, IL include:
  • Memorial Day, the unofficial start of summer with vibrant outdoor activities and events
  • Independence Day, spectacular fireworks and festive celebrations throughout the city
  • Labor Day, a lively atmosphere with various festivals and pleasant weather.
The best season to visit Chicago, IL is Spring or Summer. The best weather to explore Chicago, IL is during May-September.
For domestic flights we recommend to arrive 1.5 to 2 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.
Most airlines permit carry-on bags that fit within specific dimensions (e.g., 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.
Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs). Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you. Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.

popular airports

Popular airports from Madison, WI to Chicago, IL

Madison
Chicago
The major airport for departures in Madison is Dane County Regional Airport. Find all the information you need to know about services, amenities and connections at Dane County Regional Airport for your trip from Madison to Chicago.
Dane County Regional Airport (MSN)
information

More options for your journey from Madison, WI to Chicago, IL

Here are some other resources that might have the information you need

Return journeys for flights from Chicago, IL to Madison, WI
Buses from Madison, WI to Chicago, IL
More information on flights to Madison, WI
More information on flights to Chicago, IL

Most popular flights to and from Chicago, IL and Madison, WI

Flights Madison, WI - New York, NY
Flights Madison, WI - Kansas City, MO
Flights Madison, WI - Alajuela
Flights Madison, WI - Grand Rapids, MI
Flights Madison, WI - Louisville, KY
Flights Madison, WI - Saint Paul, MN
Flights Madison, WI - Omaha, NE
Flights Madison, WI - Independence, MO
Flights Madison, WI - Pensacola, FL
Flights Madison, WI - McAllen, TX
Flights Madison, WI - Montgomery, AL
Flights Madison, WI - College Station, TX
Flights Madison, WI - Auburn Hills, MI
Flights Madison, WI - Los Angeles, CA
Flights Madison, WI - Marrickville
Flights Madison, WI - Washington, DC
Flights Madison, WI - Boston, MA
Flights Madison, WI - Funza
Flights Madison, WI - El Rosario
Flights Madison, WI - Miami, FL
Flights Madison, WI - Melbourne
Flights Madison, WI - Wynnum
Flights New York, NY - Chicago, IL
Flights London - Chicago, IL
Flights Paris - Chicago, IL
Flights Madrid - Chicago, IL
Flights Los Angeles, CA - Chicago, IL
Flights Berlin - Chicago, IL
Flights Dubai - Chicago, IL
Flights Barcelona - Chicago, IL
Flights Rome - Chicago, IL
Flights Washington, DC - Chicago, IL
Flights Boston, MA - Chicago, IL
Flights Funza - Chicago, IL
Flights El Rosario - Chicago, IL
Flights Amsterdam - Chicago, IL
Flights Miami, FL - Chicago, IL
Flights San Diego, CA - Chicago, IL
Flights Las Vegas, NV - Chicago, IL
Flights Seattle, WA - Chicago, IL
Flights Paris Charles de Gaulle Airport - Chicago, IL
Flights Atlanta, GA - Chicago, IL
Flights Munich - Chicago, IL
Flights Brussels - Chicago, IL
HomeFlightsFlights in USAFlight Schedules to Chicago, ILMadison, WI to Chicago, IL Flights

The Omio App Makes Travel Planning Easy

We’ll get you where you want to go. From live train updates to mobile tickets, our innovative app is the ideal way to plan and keep track of your travel.

ios-badge
android-badge
Hand With Phone