What are the most exciting events happening in 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.

What are the best holidays to spend in Chicago, IL?

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.

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Madison, WI to Chicago, IL flight with Republic Airlines

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Journey information

Overview: Madison, WI to Chicago, IL flight

USA

Flights from Madison, WI to Chicago, IL depart on average 13 times per day, taking around 1h 32m. Cheap flight tickets for this journey start at $134 (€112) but you can travel from only $35 (€29) by bus.

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 $35 (€29)

Distance

122 miles (197 km)

Average flight duration

1h 32m

Cheapest ticket price

$134 (€112)

Flights per day

Direct flights

Airlines

Fastest flight

1h 4m

Cheapest month to travel

November

First flight

05:00

Last flight

21:52

Price information

Cheapest alternative travel mode

Bus from $35 (€29)

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

Showing times and prices for May 15

Cheapest price

$261

Average price

$301

Fastest journey

1 h 12 m

Average duration

1 h 13 m

Flights per day

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 $301 if you buy it on the day, but the cheapest tickets can be found for only $261.

Fast flights

Of the 3 flights that leave Madison, WI for Chicago, IL onThu, May 15, 3 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.

On Thu, May 15 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 12 m .

On Thu, May 15 the longest flights will take 1 h 13 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.

11:00AM1h13

Madison, WI

12:13PMChicago, IL

$2611One-way

0 transfers

09:53PM1h12

Madison, WI

11:05PMChicago, IL

$3191One-way

0 transfers

12:30PM1h13

Madison, WI

01:43PMChicago, IL

$3211One-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 €29. For those with little time consider booking a flight which can get you there in 1h 32m.

Compare flight with

Flight	Most popular Bus
€251 Average price	€37 Average price Cheapest
4h 32m Average duration Fastest 1h 32m Onboard + 3h 0m Additional time*	3h 58m Average duration 3h 28m Onboard + 30m Additional time*
Direct Options	Direct Options

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 $263

Buses

from $32

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

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May 15

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FAQs: Madison, WI to Chicago, IL Flight

FAQs: Take a flight from Madison, WI to Chicago, IL hassle-free. Whether you want fast, cheap or something entirely different, our travel experts have collected everything you need to know so you can find the best option from Madison, WI to Chicago, IL.

Cheap plane tickets from Madison, WI to Chicago, IL can start from as little as $133 (€112) when you book in advance. The average flight ticket price for Madison, WI to Chicago, IL is $275 (€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.

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