- Must visit
Art Institute of Chicago
One of the oldest and largest art museums in the US, known for its collection of Impressionist and Post-Impressionist paintings.
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Journey information
Overview: Winona, MN to Chicago, IL flight
USAUSA
Flights from Winona, MN to Chicago, IL depart on average 2 times per day, taking around 1h 31m. Cheap flight tickets for this journey start at $252 (€204) but you can travel from only $39 (€32) by train.
There are 2 flights per day. The earliest flight runs at 05:00, the last at 23:00. The fastest flight covers the 252 miles (406 km) distance in 1h 26m. August 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
Train from $39 (€32)
Distance 252 miles (406 km) |
Average flight duration 1h 31m |
Cheapest ticket price $252 (€204) |
Flights per day 2 |
Direct flights 2 |
Fastest flight 1h 26m |
First flight 5:00 AM |
Last flight 11:00 PM |
Cheapest Month Aug |
Cheapest Day Tue |
High Season Oct - Dec |
Low Season Apr - Jun |
Busiest Day Tue |
Least Busy Day Mon |
Best time to book 63 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
Train from $39 (€32)
The cheapest and fastest flights from Winona, MN to Chicago, IL
Showing times and prices for May 20
Cheapest price
$382
Average price
$395
Fastest journey
1 h 27 m
Average duration
1 h 32 m
Flights per day
5
Distance
406 km
Cheap tickets
The best way to find a cheap flight ticket from Winona, MN 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 Winona, MN to Chicago, IL will cost around $395 if you buy it on the day, but the cheapest tickets can be found for only $382.
Fast flights
Of the 5 flights that leave Winona, MN for Chicago, IL onWed, May 20, 5 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, May 20 the direct flights cover the 406 km distance in an average of 1 h 32 m but if you time it right, some flights will get you there in just 1 h 27 m .
On Wed, May 20 the longest flights will take 1 h 39 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.
12:37 AM1h29Winona, MN2:06 AMChicago, IL$3821One-way0 transfers- 10:53 AM1h27Winona, MN12:20 PMChicago, IL$3881One-way0 transfers
- 11:36 PM1h29Winona, MN1:05 AMChicago, IL$3891One-way0 transfers
- 10:40 AM1h39Winona, MN12:19 PMChicago, IL$4071One-way0 transfers
- 1:00 PM1h38Winona, MN2:38 PMChicago, IL$4081One-way0 transfers
- 10:53 AM1h27Winona, MN12:20 PMChicago, IL$3881One-way0 transfers
- 12:37 AM1h29Winona, MN2:06 AMChicago, IL$3821One-way0 transfers
- 11:36 PM1h29Winona, MN1:05 AMChicago, IL$3891One-way0 transfers
- 1:00 PM1h38Winona, MN2:38 PMChicago, IL$4081One-way0 transfers
- 10:40 AM1h39Winona, MN12:19 PMChicago, IL$4071One-way0 transfers
Travel Information
Compare train, bus, and flight for Winona, MN to Chicago, IL
Omio recommends booking the train as it is the most popular option from Winona, MN to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $39. For those with little time consider booking a flight which can get you there in 1h 31m. The ticket price range depends on the travel mode: a train costs an average of $39, and a flight costs an average of $252.
Distance: 252 miles (406 km)
Compare flight with
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
$420 Average price | $86 Average price Cheapest | $116 Average price | $67 Average price (fuel + tolls) |
4h 31m Average total duration Fastest 1h 31m Onboard + 3h 0m Additional time* | 6h 10m Average total duration 5h 40m Onboard + 30m Additional time* | 7h 50m Average total duration 7h 20m Onboard + 30m Additional time* | 4h 29m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Winona, MN to Chicago, IL is a train with an average price of $86 (€70).
This is compared to other travel options from Winona, MN to Chicago, IL:
A train is $29 (€24) less than a bus for this route with tickets for a bus from Winona, MN to Chicago, IL costing on average $116 (€93).
A train is $333 (€269) less than a flight for this route with tickets for a flight from Winona, MN to Chicago, IL costing on average $420 (€339).
The fastest way to travel from Winona, MN to Chicago, IL is by flight with an average journey time of 1h 31m.
Other travel options to Chicago, IL take longer:
Train takes on average 5h 40m.
Bus takes on average 7h 20m.
It's helpful to compare your options as there are 3 ways to travel between Winona, MN and Chicago, IL including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Winona, MN to Chicago, IL among Omio's users.
Live departures
Winona, MN to Chicago, IL flight times
The table below shows live departures for Winona, MN to Chicago, IL flights for today, Monday, May 18. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 4:36 PM Winona, MN | 1h35 | 6:11 PM Chicago, IL | 0 transfersDirect | |
| 4:37 PM Winona, MN | 1h26 | 6:03 PM Chicago, IL | 0 transfersDirect | |
| 5:33 PM Winona, MN | 1h26 | 6:59 PM Chicago, IL | 0 transfersDirect | |
| Tuesday, May 19 | |||||
| 12:37 AM Winona, MN | 1h29 | 2:06 AM Chicago, IL | 0 transfersDirect | |
| 10:40 AM Winona, MN | 1h39 | 12:19 PM Chicago, IL | 0 transfersDirect | |
| 10:53 AM Winona, MN | 1h27 | 12:20 PM Chicago, IL | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Winona, MN to Chicago, IL by train, bus, or flight
Compare train, 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.
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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.
- Recommended
Museum of Science and Industry
The largest science museum in the Western Hemisphere, featuring interactive exhibits and a full-size replica coal mine.
- Recommended
Field Museum
A natural history museum notable for housing Sue, the most complete T. rex skeleton ever discovered.
- Must visit
The Magnificent Mile
A premier commercial district, offering luxury shopping, restaurants, and hotels along Michigan Avenue.
- Must visit
Lincoln Park
Home to attractions like the Lincoln Park Zoo and Conservatory, offering lovely green spaces for walks.
- Must visit
Grant Park
Known as ‘Chicago’s front yard,’ it hosts major events and festivals, and houses Museum Campus.
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: Winona, MN to Chicago, IL Flight
Find answers to the most common questions about traveling from Winona, MN 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 Winona, MN to Chicago, IL can start from as little as $252 (€204) when you book in advance. The average flight ticket price for Winona, MN to Chicago, IL is $420 (€339) ; 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 Winona, MN to Chicago, IL is 1h 26m to travel the 252 miles (406 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 Winona, MN to Chicago, IL leaves at 5:00 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Winona, MN to Chicago, IL leaves at 11:00 PM.
The cheapest month for a flight from Winona, MN to Chicago, IL is August.
It's helpful to compare your options as there are 3 ways to travel between Winona, MN and Chicago, IL including taking a train, bus, and flight.
Since neither Winona, MN 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 Winona, MN 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.
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 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 train as it is the most popular way to get from Winona, MN 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 Winona, MN to Chicago, IL
Winona
Chicago
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 Winona, MN to Chicago, IL
Here are some other resources that might have the information you need
Most popular flights to and from Chicago, IL and Winona, MN
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