- Must visit
The Art Institute Of Chicago
One of the premier art museums in the United States, known for its Impressionist masterpieces, modern works, and iconic collections in a landmark downtown building.
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Journey information
Overview: Madison, WI to Chicago, IL flight
USAUSA
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 $220 (€177) but you can travel from only $24 (€20) by bus.
There are 9 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 3m. October 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 $24 (€20)
Distance 123 miles (198 km) |
Average flight duration 1h 11m |
Cheapest ticket price $220 (€177) |
Flights per day 19 |
Direct flights 9 |
Fastest flight 1h 3m |
First flight 12:02 AM |
Last flight 11:55 PM |
Cheapest Month Oct |
Cheapest Day Wed |
High Season Jul - Sep |
Low Season Jan - Mar |
Busiest Day Mon |
Least Busy Day Sun |
Best time to book 28 days |
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 $24 (€20)
The cheapest and fastest flights from Madison, WI to Chicago, IL
Showing times and prices for Jun 01
Cheapest price
$380
Average price
$603
Fastest journey
1 h 9 m
Average duration
1 h 10 m
Flights per day
24
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 $603 if you buy it on the day, but the cheapest tickets can be found for only $380.
Fast flights
Of the 24 flights that leave Madison, WI for Chicago, IL onMon, Jun 01, 12 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, Jun 01 the direct flights cover the 198 km distance in an average of 1 h 10 m but if you time it right, some flights will get you there in just 1 h 9 m .
On Mon, Jun 01 the longest flights will take 1 h 12 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.
UA535810:40 AM1h17Dane County Regional Airport11:57 AMO'Hare International Airport$3801One-way0 transfers- UA21518:05 AM1h10Dane County Regional Airport9:15 AMO'Hare International Airport$3801One-way0 transfers
- UA21376:30 AM1h10Dane County Regional Airport7:40 AMO'Hare International Airport$3801One-way0 transfers
- UA46035:45 PM1h15Dane County Regional Airport7:00 PMO'Hare International Airport$3801One-way0 transfers
- UA5293:53 PM1h12Dane County Regional Airport5:05 PMO'Hare International Airport$3801One-way0 transfers
AA64945:00 AM1h09Dane County Regional Airport6:09 AMO'Hare International Airport$3801One-way0 transfers- UA21518:05 AM1h10Dane County Regional Airport9:15 AMO'Hare International Airport$3801One-way0 transfers
- UA21376:30 AM1h10Dane County Regional Airport7:40 AMO'Hare International Airport$3801One-way0 transfers
- UA559812:24 PM1h11Dane County Regional Airport1:35 PMO'Hare International Airport$3801One-way0 transfers
- UA5293:53 PM1h12Dane County Regional Airport5:05 PMO'Hare International Airport$3801One-way0 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 $24. 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 $24, and a flight costs an average of $220.
Distance: 123 miles (198 km)
Compare flight with
| Flight | Most popular Bus | Train | Driving |
|---|---|---|---|
$362 Average price | $42 Average price Cheapest | $67 Average price | $35 Average price (fuel + tolls) |
4h 11m Average total duration Fastest 1h 11m Onboard + 3h 0m Additional time* | 3h 56m Average total duration 3h 26m Onboard + 30m Additional time* | 3h 28m Average total duration 2h 58m Onboard + 30m Additional time* | 2h 21m Average total duration (door-to-door) |
 Most popular airline |  Most popular bus company |  Most popular train company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Madison, WI to Chicago, IL is a bus with an average price of $42 (€33).
This is compared to other travel options from Madison, WI to Chicago, IL:
A bus is $26 (€21) less than a train for this route with tickets for a train from Madison, WI to Chicago, IL costing on average $67 (€54).
A bus is $320 (€258) less than a flight for this route with tickets for a flight from Madison, WI to Chicago, IL costing on average $362 (€291).
The fastest way to travel from Madison, WI to Chicago, IL is by flight with an average journey time of 1h 11m.
Other travel options to Chicago, IL take longer:
Train takes on average 2h 58m.
Bus takes on average 3h 26m.
It's helpful to compare your options as there are 3 ways to travel between Madison, WI and Chicago, IL including taking a bus, flight, and train.
We recommend using the bus as it is the most popular way to get from Madison, WI to Chicago, IL among Omio's users.
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, May 31. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| UA4392 | 2:35 PM Dane County Regional Airport | 1h11 | 3:46 PM O'Hare International Airport | 0 transfersDirect | |
 AA3716 | 2:40 PM Dane County Regional Airport | 1h14 | 3:54 PM O'Hare International Airport | 0 transfersDirect | |
| UA2338 · UA2258 | 3:10 PM Dane County Regional Airport | 7h39 | 10:49 PM O'Hare International Airport | 1 transfer | |
| UA2338 · UA1672 | 3:10 PM Dane County Regional Airport | 9h40 | 12:50 AM O'Hare International Airport | 1 transfer | |
| UA2338 · UA1411 | 3:10 PM Dane County Regional Airport | 6h44 | 9:54 PM O'Hare International Airport | 1 transfer | |
| UA529 | 3:53 PM Dane County Regional Airport | 1h12 | 5:05 PM O'Hare International Airport | 0 transfersDirect | |
| UA4603 | 5:45 PM Dane County Regional Airport | 1h15 | 7:00 PM O'Hare International Airport | 0 transfersDirect | |
| UA5567 · UA1430 | 5:49 PM Dane County Regional Airport | 6h55 | 12:44 AM O'Hare International Airport | 1 transfer | |
| AA3717 | 6:44 PM Dane County Regional Airport | 1h21 | 8:05 PM O'Hare International Airport | 0 transfersDirect | |
| Monday, June 1 | |||||
| UA5545 · UA2430 | 5:00 AM Dane County Regional Airport | 6h44 | 11:44 AM O'Hare International Airport | 1 transfer | |
| UA5545 · UA1928 | 5:00 AM Dane County Regional Airport | 6h23 | 11:23 AM O'Hare International Airport | 1 transfer | |
| UA5545 · UA2329 | 5:00 AM Dane County Regional Airport | 8h15 | 1:15 PM O'Hare International Airport | 1 transfer | |
| AA6494 | 5:00 AM Dane County Regional Airport | 1h09 | 6:09 AM O'Hare International Airport | 0 transfersDirect | |
| UA3482 · UA2053 | 6:24 AM Dane County Regional Airport | 8h19 | 2:43 PM O'Hare International Airport | 1 transfer | |
| UA3482 · UA1875 | 6:24 AM Dane County Regional Airport | 6h44 | 1:08 PM O'Hare International Airport | 1 transfer | |
| UA2137 | 6:30 AM Dane County Regional Airport | 1h10 | 7:40 AM O'Hare International Airport | 0 transfersDirect | |
| AA4688 | 6:30 AM Dane County Regional Airport | 1h21 | 7:51 AM O'Hare International Airport | 0 transfersDirect | |
| UA2151 | 8:05 AM Dane County Regional Airport | 1h10 | 9:15 AM O'Hare International Airport | 0 transfersDirect | |
| AA4018 | 8:19 AM Dane County Regional Airport | 1h24 | 9:43 AM O'Hare International Airport | 0 transfersDirect | |
| UA2360 · UA2865 | 8:50 AM Dane County Regional Airport | 6h05 | 2:55 PM O'Hare International Airport | 1 transfer | |
| UA2360 · UA617 | 8:50 AM Dane County Regional Airport | 8h15 | 5:05 PM O'Hare International Airport | 1 transfer | |
| UA5358 | 10:40 AM Dane County Regional Airport | 1h17 | 11:57 AM O'Hare International Airport | 0 transfersDirect | |
| UA3675 · UA661 | 10:52 AM Dane County Regional Airport | 7h42 | 6:34 PM O'Hare International Airport | 1 transfer | |
| AA3437 | 12:06 PM Dane County Regional Airport | 1h15 | 1:21 PM O'Hare International Airport | 0 transfersDirect | |
| UA5598 | 12:24 PM Dane County Regional Airport | 1h11 | 1:35 PM O'Hare International Airport | 0 transfersDirect | |
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 $273Buses
from $34Compare 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 from Madison, WI to Chicago, ILFind the best flights between Madison, WI to Chicago, IL with Omio's travel partners Republic Airlines from $24 (€20). 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
$272 (€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.
Complete guide to Chicago
Things to do in Chicago
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
- Must visit
Field Museum
A world-class natural history museum famous for its dinosaur fossils, ancient cultures, and major scientific collections, including the celebrated T. rex specimen SUE.
- Must visit
Museum Of Science And Industry
A large interactive science museum in Hyde Park with hands-on exhibits, transportation displays, and family-friendly experiences in a grand historic building.
- Must visit
Millennium Park
Chicago’s signature downtown park combines major public art, gardens, and event spaces, making it one of the city’s essential first stops for visitors.
- Must visit
The Magnificent Mile
The city’s best-known stretch of Michigan Avenue is lined with landmark buildings, shops, and hotels, and serves as a central walking route for first-time visitors.
- Must visit
Chicago Riverwalk
A highly popular waterfront promenade with excellent architecture views, bridges, and easy access to boat tours. It is one of the city’s most scenic urban walks.
Deep-Dish Pizza
Chicago’s iconic thick, buttery-crust pizza baked in a deep pan with layers of cheese, toppings, and chunky tomato sauce.
Chicago-Style Hot Dog
An all-beef hot dog on a poppy seed bun topped with mustard, onions, relish, tomato, pickle spear, sport peppers, and celery salt.
Italian Beef Sandwich
Thin-sliced seasoned roast beef served on a long roll, often dipped in jus and topped with sweet peppers or giardiniera.
Girl & the Goat
A celebrated West Loop restaurant with bold small plates, creative flavors, and a vibrant, modern atmosphere.
Alinea
Chicago’s internationally renowned fine-dining destination known for highly creative tasting menus and theatrical presentation.
Lou Malnati's Pizzeria
A classic Chicago pizzeria famous for buttery-crust deep-dish pizza and a relaxed, family-friendly atmosphere.
United States Dollar
Moderate for a major U.S. city: casual food is reasonable, but hotels, parking, and fine dining add up fast.
Average meal costs
- Budget
- USD 10-18 for fast food or casual takeout.
- Mid-range
- USD 25-45 per person at a mid-range restaurant.
- Fine dining
- USD 80+ per person before drinks and tip.
- Coffee
- USD 4-7 for a coffee drink.
Tipping culture
Tip 18-20% at restaurants; 20%+ for great service. Bars: USD 1-2 per drink. Taxis/rideshares: 10-15%. Hotels: USD 2-5 for housekeeping; USD 1-2 per bag.
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 $220 (€177) when you book in advance. The average flight ticket price for Madison, WI to Chicago, IL is $362 (€291) ; 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 3m 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 9 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 October.
It's helpful to compare your options as there are 3 ways to travel between Madison, WI and Chicago, IL including taking a bus, flight, and train.
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.
Some of the most interesting sights to explore in Chicago, IL are:
- Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
- Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
- Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
- Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
- Field Museum, a natural history museum with vast exhibits including the famous T. rex skeleton, Sue.
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 things to do in Chicago, IL include:
- Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
- Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
- Take a river cruise to see the city's iconic architecture from a different perspective
- Attend a live performance at the historic Chicago Theatre
- Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U.S., offering free admission.
The best season to visit Chicago, IL is Spring or Summer. The best weather to explore Chicago, IL is during May-September.
We recommend using the bus as it is the most popular way to get from Madison, WI to Chicago, IL among Omio's users.
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.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
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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