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Journey information
Overview: Madison, WI to Chicago, IL flight
USAUSA
Flights from Madison, WI to Chicago, IL depart on average 15 times per day, taking around 1h 8m. Cheap flight tickets for this journey start at $222 (€180) but you can travel from only $27 (€22) by bus.
There are 5 flights per day. The earliest flight runs at 00:30, the last at 23:55. The fastest flight covers the 123 miles (198 km) distance in 1h 0m. March 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 (€22)
Distance 123 miles (198 km) |
Average flight duration 1h 8m |
Cheapest ticket price $222 (€180) |
Flights per day 15 |
Direct flights 5 |
Fastest flight 1h 0m |
Cheapest month to travel March |
First flight 00:30 |
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 (€22)
The cheapest and fastest flights from Madison, WI to Chicago, IL
Showing times and prices for Dec 02
Cheapest price
$296
Average price
$300
Fastest journey
1 h 5 m
Average duration
1 h 8 m
Flights per day
4
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 $300 if you buy it on the day, but the cheapest tickets can be found for only $296.
Fast flights
Of the 4 flights that leave Madison, WI for Chicago, IL onTue, Dec 02, 4 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Tue, Dec 02 the direct flights cover the 198 km distance in an average of 1 h 8 m but if you time it right, some flights will get you there in just 1 h 5 m .
On Tue, Dec 02 the longest flights will take 1 h 11 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.
11:44PM1h05
Madison, WI12:49AMChicago, IL
$2961One-way
0 transfers
11:41PM1h11
Madison, WI12:52AMChicago, IL
$2961One-way
0 transfers
02:41PM1h07
Madison, WI03:48PMChicago, IL
$2981One-way
0 transfers
03:10PM1h08
Madison, WI04:18PMChicago, IL
$3101One-way
0 transfers
11:44PM1h05
Madison, WI12:49AMChicago, IL
$2961One-way
0 transfers
02:41PM1h07
Madison, WI03:48PMChicago, IL
$2981One-way
0 transfers
03:10PM1h08
Madison, WI04:18PMChicago, IL
$3101One-way
0 transfers
11:41PM1h11
Madison, WI12:52AMChicago, IL
$2961One-way
0 transfers
Travel Information
Compare bus, flight, and train 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 €22. For those with little time consider booking a flight which can get you there in 1h 8m. The ticket price range depends on the travel mode: a bus costs an average of €22, and a flight costs an average of €180.
Distance: 123 miles (198 km)
Compare flight with
| Flight | Most popular Bus | Train |
|---|---|---|
€260 Average price | €31 Average price Cheapest | €52 Average price |
4h 8m Average total duration Fastest 1h 8m Onboard + 3h 0m Additional time* | 3h 58m Average total duration 3h 28m Onboard + 30m Additional time* | 3h 28m Average total duration 2h 58m Onboard + 30m Additional time* |
 Most popular airline |  Most popular bus company |  Most popular train company |
Direct Options | 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, Monday, December 1. You can also manually refresh the results below to see updated flight journeys.
Last updated at 12:27 PM
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
 UA2137 | 12:30 PM Dane County Regional Airport | 1h11 | 1:41 PM O'Hare International Airport | 0 transfersDirect | |
 AA6190 | 1:00 PM Dane County Regional Airport | 1h16 | 2:16 PM O'Hare International Airport | 0 transfersDirect | |
| UA2364 | 2:25 PM Dane County Regional Airport | 1h11 | 3:36 PM O'Hare International Airport | 0 transfersDirect | |
| UA2748 · UA1923 | 2:30 PM Dane County Regional Airport | 11h10 | 1:40 AM O'Hare International Airport | 1 transfer | |
| UA2748 · UA617 | 2:30 PM Dane County Regional Airport | 8h28 | 10:58 PM O'Hare International Airport | 1 transfer | |
| UA2748 · UA1411 | 2:30 PM Dane County Regional Airport | 12h28 | 2:58 AM O'Hare International Airport | 1 transfer | |
| UA2748 · UA2258 | 2:30 PM Dane County Regional Airport | 14h20 | 4:50 AM O'Hare International Airport | 1 transfer | |
| UA2748 · UA2865 | 2:30 PM Dane County Regional Airport | 6h18 | 8:48 PM O'Hare International Airport | 1 transfer | |
| UA2748 · UA377 | 2:30 PM Dane County Regional Airport | 15h28 | 5:58 AM O'Hare International Airport | 1 transfer | |
| UA2748 · UA1023 | 2:30 PM Dane County Regional Airport | 10h23 | 12:53 AM O'Hare International Airport | 1 transfer | |
 AA4243 | 3:55 PM Dane County Regional Airport | 1h14 | 5:09 PM O'Hare International Airport | 0 transfersDirect | |
| UA4491 | 4:35 PM Dane County Regional Airport | 1h14 | 5:49 PM O'Hare International Airport | 0 transfersDirect | |
| UA5383 | 6:18 PM Dane County Regional Airport | 1h12 | 7:30 PM O'Hare International Airport | 0 transfersDirect | |
| AA6217 | 7:14 PM Dane County Regional Airport | 1h13 | 8:27 PM O'Hare International Airport | 0 transfersDirect | |
| UA5783 | 8:48 PM Dane County Regional Airport | 1h15 | 10:03 PM O'Hare International Airport | 0 transfersDirect | |
| UA1464 · UA377 | 9:08 PM Dane County Regional Airport | 8h50 | 5:58 AM O'Hare International Airport | 1 transfer | |
| UA1464 · UA2258 | 9:08 PM Dane County Regional Airport | 7h42 | 4:50 AM O'Hare International Airport | 1 transfer | |
| UA1464 · UA1411 | 9:08 PM Dane County Regional Airport | 5h50 | 2:58 AM O'Hare International Airport | 1 transfer | |
| UA1193 | 9:58 PM Dane County Regional Airport | 1h11 | 11:09 PM O'Hare International Airport | 0 transfersDirect | |
 AA5651 | 10:32 PM Dane County Regional Airport | 1h17 | 11:49 PM O'Hare International Airport | 0 transfersDirect | |
| UA5392 | 11:38 PM Dane County Regional Airport | 1h09 | 12:47 AM O'Hare International Airport | 0 transfersDirect | |
| UA5767 · UA1811 | 11:48 PM Dane County Regional Airport | 17h41 | 5:29 PM O'Hare International Airport | 1 transfer | |
| UA5767 · UA377 | 11:48 PM Dane County Regional Airport | 6h10 | 5:58 AM O'Hare International Airport | 1 transfer | |
| UA5767 · UA1377 | 11:48 PM Dane County Regional Airport | 15h52 | 3:40 PM O'Hare International Airport | 1 transfer | |
| Tuesday, December 2 | |||||
| UA5784 | 12:50 AM Dane County Regional Airport | 1h14 | 2:04 AM O'Hare International Airport | 0 transfersDirect | |
| AA6356 | 2:12 AM Dane County Regional Airport | 1h18 | 3:30 AM O'Hare International Airport | 0 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.
Flights
from $272Buses
from $33Compare prices and tickets Madison, WI to Chicago, IL by bus, flight, or train
Compare bus, flight, and train 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.
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Airlines: Republic Airlines, air wisconsin from Madison, WI to Chicago, ILFind the best flights between Madison, WI to Chicago, IL with Omio's travel partners Republic Airlines, air wisconsin from $27 (€22). We can find you the best deals, schedules and tickets when comparing and booking the best trip.
air wisconsin
About
Air Wisconsin Airlines is a regional airline founded in 1965 and headquartered in Greenville, Wisconsin. It has a long history of operating as a feeder carrier for major airlines, including United Express, US Airways Express, and American Eagle. Air Wisconsin operates flights throughout the Midwest and East Coast, connecting smaller cities to larger hubs. The airline is known for its focus on safety, service, and making smart business decisions in a dynamic industry. As of April 2025, Air Wisconsin is transitioning to primarily flying charter and Essential Air Service subsidized flights.
Luggage & cancellation policy
Luggage included
One carry-on bag (22 x 14 x 9 inches) and one personal item (17 x 10 x 9 inches) are allowed for standard economy and higher fares; Basic Economy only allows one personal item. Checked bags cannot exceed 50lbs and 62 linear inches.
Additional luggage
Additional checked bags are allowed with fees: $50 for the second bag and $50 for the third bag, with overweight charges for bags between 50-75 lbs.
Cancellation Policy
A refund may be requested for an unused reservation, or portion of a reservation, by contacting the reservations center; full fare and fees will be refunded if no part of the reservation has been flown, otherwise, a partial refund can be requested before the originally scheduled departure time.
Refund
If your flight is canceled and you choose not to travel, you are entitled to a full refund.
Unaccompagned minor
Unaccompanied minor service is mandatory for children between the ages of 5 and 15.
Amenities on board the airplane
Seat reservation
Standard seats can typically be selected at check-in at no extra cost, while preferred seating or extra legroom (Economy Plus) are available for an additional fee during booking or check-in.
Toilets
Accessibility
Bikes
Bicycles must be in a hard-sided bicycle box or container with handlebars turned sideways, and protruding pedals and accessories removed.
Pets
Only domesticated cats and dogs are allowed in the cabin, with a maximum combined weight of 20 lbs for the pet and carrier, and the carrier must fit under the seat.
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
$271 (€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
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.
Cheap plane tickets from Madison, WI to Chicago, IL can start from as little as $138 (€112) when you book in advance. The average flight ticket price for Madison, WI to Chicago, IL is $286 (€231); 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 1 h 1 min to travel the 122 mile (197 km) long trip, with around there are 13 flights per day. Journey times can vary on weekends and holidays.
The earliest flight from Madison, WI to Chicago, IL leaves at 5: 00AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Madison, WI to Chicago, IL leaves at 9: 52PM.
There are 13 flights a day from Madison, WI to Chicago, IL which require at least one change with Republic Airlines. Schedules can vary on holidays or weekends with fewer flights.
Take the Madison, WI to Chicago, IL flight with Republic Airlines. However, it's always good to check out all possible airlines for the trip between Madison, WI and Chicago, IL as there might be differences in the amenities they offer.
The cheapest month for a flight from Madison, WI to Chicago, IL is November.
You have options as you can travel from Madison, WI to Chicago, IL 2 different ways: bus or flight.
Since neither Madison, WI nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of USA and USA. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
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 seasons to visit Chicago, IL are 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.
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
The major airport for arrivals in Chicago is O'Hare International Airport. Find all the information you need to know about services, amenities and connections at O'Hare International Airport for your journey to Chicago from Madison.
Amenities at airport
Wifi
Shopping
Parking
Dining
ATM
Taxis
Accessibility
WC
Hotel
Shower
Lounge
Lost and Found Office
Car Rentalinformation
Distance to city center
3 km
Car connection
I-190, Exit 1Wifi
- Free Wi-Fi available throughout the airport.
Shopping
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
Parking
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
Dining
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Taxis
- Available outside the terminal.
Accessibility
- Elevators, ramps, toilets
WC
- Available throughout the airport.
Hotel
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
Shower
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
Lounge
- Lounges available, including United Club and American Airlines Admirals Club.
Lost and Found Office
- Lost and Found located in terminal 1, near the baggage claim area.
Car Rental
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis.
Public transit options for O'Hare International Airport
- CTA Blue Line, O'Hare Station, 45 minutes to city center
More options for your journey from Madison, WI to Chicago, IL
Here are some other resources that might have the information you need
Most popular flights to and from Chicago, IL and Madison, WI
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