- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
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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 €204 but you can travel from only €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 €32
Distance 252 miles (406 km) |
Average flight duration 1h 31m |
Cheapest ticket price €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 €32
The cheapest and fastest flights from Winona, MN to Chicago, IL
Showing times and prices for Aug 04
Cheapest price
€339
Average price
€339
Fastest journey
1 h 24 m
Average duration
1 h 39 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 €339 if you buy it on the day, but the cheapest tickets can be found for only €339.
Fast flights
Of the 5 flights that leave Winona, MN for Chicago, IL onTue, Aug 04, 5 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Tue, Aug 04 the direct flights cover the 406 km distance in an average of 1 h 39 m but if you time it right, some flights will get you there in just 1 h 24 m .
On Tue, Aug 04 the longest flights will take 1 h 58 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.
AA36455:57 PM1h41La Crosse Regional Airport7:38 PMO'Hare International Airport€3391One-way0 transfers- AA417410:59 AM1h30Rochester International Airport12:29 PMO'Hare International Airport€3391One-way0 transfers
- AA364912:01 PM1h24La Crosse Regional Airport1:25 PMO'Hare International Airport€3391One-way0 transfers
AA63385:46 AM1h44Rochester International Airport7:30 AMO'Hare International Airport€3391One-way0 transfers- AA62917:02 PM1h58Rochester International Airport9:00 PMO'Hare International Airport€3391One-way0 transfers
- AA364912:01 PM1h24La Crosse Regional Airport1:25 PMO'Hare International Airport€3391One-way0 transfers
- AA417410:59 AM1h30Rochester International Airport12:29 PMO'Hare International Airport€3391One-way0 transfers
- AA36455:57 PM1h41La Crosse Regional Airport7:38 PMO'Hare International Airport€3391One-way0 transfers
- AA63385:46 AM1h44Rochester International Airport7:30 AMO'Hare International Airport€3391One-way0 transfers
- AA62917:02 PM1h58Rochester International Airport9:00 PMO'Hare International Airport€3391One-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 €32. 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 €32, and a flight costs an average of €204.
Distance: 252 miles (406 km)
Compare flight with
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
€339 Average price | €70 Average price Cheapest | €93 Average price | €54 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 €70.
This is compared to other travel options from Winona, MN to Chicago, IL:
A train is €24 less than a bus for this route with tickets for a bus from Winona, MN to Chicago, IL costing on average €93.
A train is €269 less than a flight for this route with tickets for a flight from Winona, MN to Chicago, IL costing on average €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, August 3. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
 | 10:53 AM Winona, MN | 1h27 | 12:20 PM Chicago, IL | 0 transfersDirect | |
| 12:00 PM Winona, MN | 1h39 | 1:39 PM Chicago, IL | 0 transfersDirect | |
| 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 |
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, IL
Things to do in Chicago, IL
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
- Must visit
Field Museum
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
- Must visit
Museum of Science and Industry
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
- Must visit
Millennium Park
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
- Must visit
Magnificent Mile
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
- Must visit
Chicago Riverwalk
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-Dish Pizza
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
Chicago-Style Hot Dog
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian Beef Sandwich
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Johnnie's Beef
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Superdawg Drive-In
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
Alinea
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
US dollar ($)
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Average meal costs
- Budget
- $10-18 for fast food or casual takeout.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $75+ per person for upscale restaurants.
- Coffee
- $3-6 for coffee or cappuccino.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
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 €204 when you book in advance. The average flight ticket price for Winona, MN to Chicago, IL is €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
Most Winona, MN to Chicago, IL flights use the Rochester International Airport to O'Hare International Airport airport pair. Use this guide to compare Winona, MN and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Departure airports in Winona
Arrival airports in Chicago
Which Chicago, IL airport do flights from Winona, MN arrive at?
Flights from Winona, MN to Chicago, IL arrive at O'Hare International Airport. O'Hare International Airport is 2 miles (4 km) from Chicago, IL city centre.
O'Hare International Airport (ORD)10000 W O'Hare Ave, Chicago, IL 60666, USA
City-centre transport
Getting to O'Hare International Airport from Chicago city centre
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
SubwayBlue Line · 1h 7m · €5 · every ~23 min
O'Hare International Airport airport facilities and services
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food and drink
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at O'Hare International Airport: Parking, Taxis, WC.
Bike and car services
Available at O'Hare International Airport: Car Rental.
Accessibility
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Shops, hotels and contact
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
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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