Osceola, IA to Chicago, IL Flights

Wed, Jun 17
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Journey information

Overview: Osceola, IA to Chicago, IL flight

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Icon of flight

Flights from Osceola, IA to Chicago, IL depart on average 41 times per day, taking around 1h 36m. Cheap flight tickets for this journey start at $101 (€82) but you can travel from only $52 (€42) by train.

There are 6 flights per day. The earliest flight runs at 05:00, the last at 23:00. The fastest flight covers the 321 miles (518 km) distance in 1h 28m. July 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 $52 (€42)
Distance
321 miles (518 km)
Average flight duration
1h 36m
Cheapest ticket price
$101 (€82)
Flights per day
41
Direct flights
6
Fastest flight
1h 28m
First flight
5:00 AM
Last flight
11:00 PM
Cheapest Month
Jul
Cheapest Day
Wed
High Season
Jan - Mar
Low Season
Jul - Sep
Busiest Day
Fri
Least Busy Day
Fri
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
Train from $52 (€42)

The cheapest and fastest flights from Osceola, IA to Chicago, IL

Showing times and prices for Jun 17

Cheapest price

$158

Average price

$242

Fastest journey

1 h 31 m

Average duration

1 h 35 m

Flights per day

3

Distance

518 km

Cheap tickets

The best way to find a cheap flight ticket from Osceola, IA 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 Osceola, IA to Chicago, IL will cost around $242 if you buy it on the day, but the cheapest tickets can be found for only $158.

Fast flights

Of the 3 flights that leave Osceola, IA for Chicago, IL onWed, Jun 17, 3 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.

On Wed, Jun 17 the direct flights cover the 518 km distance in an average of 1 h 35 m but if you time it right, some flights will get you there in just 1 h 31 m .

On Wed, Jun 17 the longest flights will take 1 h 42 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.

  • American Airlines
    6:37 PM1h31
    Osceola, IA
    8:08 PMChicago, IL
    $1581One-way
    0 transfers
  • American Airlines
    12:07 PM1h42
    Osceola, IA
    1:49 PMChicago, IL
    $2341One-way
    0 transfers
  • United
    8:21 PM1h32
    Osceola, IA
    9:53 PMChicago, IL
    $3361One-way
    0 transfers

Travel Information

Compare train and flight for Osceola, IA to Chicago, IL

Omio recommends booking the train as it is the most popular option from Osceola, IA to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $52. For those with little time consider booking a flight which can get you there in 1h 36m. The ticket price range depends on the travel mode: a train costs an average of $52, and a flight costs an average of $101.

Distance: 321 miles (518 km)

Compare flight with

Flight
Most popular
Train
Driving

$268

Average price

$107

Average price

Cheapest

$86

Average price

(fuel + tolls)

4h 36m

Average total duration

Fastest

1h 36m

Onboard

+

3h 0m

Additional time*

7h 29m

Average total duration

6h 59m

Onboard

+

30m

Additional time*

5h 51m

Average total duration

(door-to-door)

Direct Options

Direct Options

Direct Options

The cheapest way to travel from Osceola, IA to Chicago, IL is a train with an average price of $107 (€86).

This is compared to other travel options from Osceola, IA to Chicago, IL:

A train is $162 (€131) less than a flight for this route with tickets for a flight from Osceola, IA to Chicago, IL costing on average $268 (€217).

The fastest way to travel from Osceola, IA to Chicago, IL is by flight with an average journey time of 1h 36m.

Other travel options to Chicago, IL take longer:

Train takes on average 6h 59m.

It's helpful to compare your options as there are 2 ways to travel between Osceola, IA and Chicago, IL including taking a train and flight.
We recommend using the train as it is the most popular way to get from Osceola, IA to Chicago, IL among Omio's users.

Live departures

Osceola, IA to Chicago, IL flight times

The table below shows live departures for Osceola, IA to Chicago, IL flights for today, Tuesday, June 16. You can also manually refresh the results below to see updated flight journeys.

Last updated at
ProviderDepartsDurationArrivesTransfers
Tickets
UnitedUA4777 · UA23295:50 AM Des Moines International Airport
7h25
1:15 PM O'Hare International Airport1 transfer
UnitedUA4777 · UA24305:50 AM Des Moines International Airport
5h54
11:44 AM O'Hare International Airport1 transfer
UnitedUA4777 · UA28655:50 AM Des Moines International Airport
9h05
2:55 PM O'Hare International Airport1 transfer
UnitedUA4777 · UA6175:50 AM Des Moines International Airport
11h15
5:05 PM O'Hare International Airport1 transfer
UnitedUA4777 · UA19285:50 AM Des Moines International Airport
5h33
11:23 AM O'Hare International Airport1 transfer
UnitedUA4777 · UA10235:50 AM Des Moines International Airport
13h01
6:51 PM O'Hare International Airport1 transfer
UnitedUA18566:00 AM Des Moines International Airport
1h40
7:40 AM O'Hare International Airport0 transfersDirect
American AirlinesAA1852+Republic AirlinesAA44636:02 AM Des Moines International Airport
8h15
2:17 PM O'Hare International Airport1 transfer
Republic AirlinesAA4463+American AirlinesAA10416:02 AM Des Moines International Airport
6h07
12:09 PM O'Hare International Airport1 transfer
American AirlinesAA470+Republic AirlinesAA44636:02 AM Des Moines International Airport
10h58
5:00 PM O'Hare International Airport1 transfer
UnitedUA1982 · UA21976:20 AM Des Moines International Airport
15h31
9:51 PM O'Hare International Airport1 transfer
UnitedUA1982 · UA21356:20 AM Des Moines International Airport
13h56
8:16 PM O'Hare International Airport1 transfer
UnitedUA1982 · UA24586:20 AM Des Moines International Airport
10h18
4:38 PM O'Hare International Airport1 transfer
UnitedUA1982 · UA24176:20 AM Des Moines International Airport
8h31
2:51 PM O'Hare International Airport1 transfer
UnitedUA1982 · UA7876:20 AM Des Moines International Airport
16h55
11:15 PM O'Hare International Airport1 transfer
UnitedUA1982 · UA21246:20 AM Des Moines International Airport
6h09
12:29 PM O'Hare International Airport1 transfer
UnitedUA1982 · UA28276:20 AM Des Moines International Airport
11h02
5:22 PM O'Hare International Airport1 transfer
American AirlinesAA489+psa airlinesAA56456:30 AM Des Moines International Airport
6h27
12:57 PM O'Hare International Airport1 transfer
American AirlinesAA2854 · AA25306:55 AM Des Moines International Airport
7h28
2:23 PM O'Hare International Airport1 transfer
American AirlinesAA2854 · AA20806:55 AM Des Moines International Airport
8h53
3:48 PM O'Hare International Airport1 transfer
American AirlinesAA2854 · AA29086:55 AM Des Moines International Airport
5h25
12:20 PM O'Hare International Airport1 transfer
American AirlinesAA2854 · AA29076:55 AM Des Moines International Airport
9h48
4:43 PM O'Hare International Airport1 transfer
Republic AirlinesAA4795+American AirlinesAA14787:10 AM Des Moines International Airport
12h10
7:20 PM O'Hare International Airport1 transfer
American AirlinesAA396+Republic AirlinesAA47957:10 AM Des Moines International Airport
10h46
5:56 PM O'Hare International Airport1 transfer
American AirlinesAA1705+Republic AirlinesAA47957:10 AM Des Moines International Airport
8h50
4:00 PM O'Hare International Airport1 transfer
Republic AirlinesAA4795 · AA44007:10 AM Des Moines International Airport
6h55
2:05 PM O'Hare International Airport1 transfer
UnitedUA53188:00 AM Des Moines International Airport
1h41
9:41 AM O'Hare International Airport0 transfersDirect
UnitedUA1521 · UA10239:14 AM Des Moines International Airport
9h37
6:51 PM O'Hare International Airport1 transfer
UnitedUA1521 · UA6759:14 AM Des Moines International Airport
10h57
8:11 PM O'Hare International Airport1 transfer
UnitedUA1521 · UA11319:14 AM Des Moines International Airport
11h16
8:30 PM O'Hare International Airport1 transfer
UnitedUA1521 · UA14119:14 AM Des Moines International Airport
12h40
9:54 PM O'Hare International Airport1 transfer
UnitedUA1521 · UA28659:14 AM Des Moines International Airport
5h41
2:55 PM O'Hare International Airport1 transfer
UnitedUA1521 · UA6179:14 AM Des Moines International Airport
7h51
5:05 PM O'Hare International Airport1 transfer
skywest airlinesAA49699:23 AM Des Moines International Airport
1h42
11:05 AM O'Hare International Airport0 transfersDirect
UnitedUA141011:26 AM Des Moines International Airport
1h37
1:03 PM O'Hare International Airport0 transfersDirect
UnitedUA5288 · UA61711:34 AM Des Moines International Airport
5h31
5:05 PM O'Hare International Airport1 transfer
UnitedUA5288 · UA67511:34 AM Des Moines International Airport
8h37
8:11 PM O'Hare International Airport1 transfer
UnitedUA5288 · UA102311:34 AM Des Moines International Airport
7h17
6:51 PM O'Hare International Airport1 transfer
UnitedUA5288 · UA225811:34 AM Des Moines International Airport
11h15
10:49 PM O'Hare International Airport1 transfer
UnitedUA5288 · UA141111:34 AM Des Moines International Airport
10h20
9:54 PM O'Hare International Airport1 transfer
UnitedUA5288 · UA113111:34 AM Des Moines International Airport
8h56
8:30 PM O'Hare International Airport1 transfer
American AirlinesAA3042+psa airlinesAA51651:33 PM Des Moines International Airport
7h57
9:30 PM O'Hare International Airport1 transfer
American AirlinesAA2840+psa airlinesAA51651:33 PM Des Moines International Airport
11h01
12:34 AM O'Hare International Airport1 transfer
UnitedUA2764 · UA6751:35 PM Des Moines International Airport
6h36
8:11 PM O'Hare International Airport1 transfer
UnitedUA2764 · UA11311:35 PM Des Moines International Airport
6h55
8:30 PM O'Hare International Airport1 transfer
UnitedUA2764 · UA14111:35 PM Des Moines International Airport
8h19
9:54 PM O'Hare International Airport1 transfer
UnitedUA2764 · UA22581:35 PM Des Moines International Airport
9h14
10:49 PM O'Hare International Airport1 transfer
American AirlinesAA1763 · AA24881:37 PM Des Moines International Airport
6h08
7:45 PM O'Hare International Airport1 transfer
American AirlinesAA1763 · AA6271:37 PM Des Moines International Airport
7h56
9:33 PM O'Hare International Airport1 transfer
Republic AirlinesAA46761:51 PM Des Moines International Airport
1h42
3:33 PM O'Hare International Airport0 transfersDirect
UnitedUA43972:49 PM Des Moines International Airport
1h35
4:24 PM O'Hare International Airport0 transfersDirect
UnitedUA6117 · UA10443:01 PM Des Moines International Airport
16h56
7:57 AM O'Hare International Airport1 transfer
UnitedUA6117 · UA7873:01 PM Des Moines International Airport
8h14
11:15 PM O'Hare International Airport1 transfer
UnitedUA6117 · UA21973:01 PM Des Moines International Airport
6h50
9:51 PM O'Hare International Airport1 transfer
American AirlinesAA2903+psa airlinesAA54283:22 PM Des Moines International Airport
6h08
9:30 PM O'Hare International Airport1 transfer
American AirlinesAA2421 · AA23464:48 PM Des Moines International Airport
6h44
11:32 PM O'Hare International Airport1 transfer
American AirlinesAA2421 · AA11934:48 PM Des Moines International Airport
7h51
12:39 AM O'Hare International Airport1 transfer
American AirlinesAA2421+envoy airAA35314:48 PM Des Moines International Airport
5h47
10:35 PM O'Hare International Airport1 transfer
UnitedUA1781 · UA22585:17 PM Des Moines International Airport
5h32
10:49 PM O'Hare International Airport1 transfer
UnitedUA1781 · UA14305:17 PM Des Moines International Airport
7h27
12:44 AM O'Hare International Airport1 transfer
UnitedUA41786:50 PM Des Moines International Airport
1h39
8:29 PM O'Hare International Airport0 transfersDirect
American AirlinesAA1762 · AA11937:02 PM Des Moines International Airport
5h37
12:39 AM O'Hare International Airport1 transfer
skywest airlinesAA49737:09 PM Des Moines International Airport
1h57
9:06 PM O'Hare International Airport0 transfersDirect
envoy airAA41028:05 PM Des Moines International Airport
1h41
9:46 PM O'Hare International Airport0 transfersDirect

This is the last flight of the day.

Find all the dates and times for this journey

Compare prices and tickets Osceola, IA to Chicago, IL by train or flight

Compare train 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.

Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
Mon
Jun 22
Tue
Jun 23

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

Art Institute Of Chicago

One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.

View on mapVisit website
  • Must visit

Field Museum

Major natural history museum known for Sue the T. rex, ancient cultures, and large family-friendly science exhibits.

View on mapVisit website
  • Must visit

Museum Of Science And Industry

Large hands-on science museum in Hyde Park with a U-505 submarine, aviation exhibits, and immersive interactive displays.

View on mapVisit website

United States Dollar

Moderate by U.S. big-city standards. Hotels can be pricey downtown, but food and transit offer good value.

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 regular café coffee.

Tipping culture

Tip 18-20% at sit-down restaurants; 20%+ for great service. USD 1-2 per drink at bars, round up or 10-15% for taxis, and USD 1-2 per bag for hotel staff.

FAQs: Osceola, IA to Chicago, IL Flight

Find answers to the most common questions about traveling from Osceola, IA 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.

FAQs
Cheap plane tickets from Osceola, IA to Chicago, IL can start from as little as $101 (€82) when you book in advance. The average flight ticket price for Osceola, IA to Chicago, IL is $268 (€217) ; 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 Osceola, IA to Chicago, IL is 1h 28m to travel the 321 miles (518 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 Osceola, IA to Chicago, IL leaves at 5:00 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Osceola, IA to Chicago, IL leaves at 11:00 PM.
The cheapest month for a flight from Osceola, IA to Chicago, IL is July.
It's helpful to compare your options as there are 2 ways to travel between Osceola, IA and Chicago, IL including taking a train and flight.
Since neither Osceola, IA 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 Osceola, IA 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 Osceola, IA 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 Osceola, IA to Chicago, IL

Osceola
Chicago
O'Hare International Airport (ORD)WifiShoppingParkingDiningATMTaxisAccessibilityWCHotelShowerLoungeLost and Found OfficeCar Rental
Amenities at airport
WifiWifi
ShoppingShopping
ParkingParking
DiningDining
ATMATM
TaxisTaxis
AccessibilityAccessibility
WCWC
HotelHotel
ShowerShower
LoungeLounge
Lost and Found OfficeLost and Found Office
Car RentalCar Rental
information
address
Address
10000 W O'Hare Ave, Chicago, IL 60666, USA
ticketOfficeHours
Distance to city center
3 km
carConnection
Car connection
I-190, Exit 1
Wifi
Wifi
  • Free Wi-Fi available throughout the airport.
Shopping
Shopping
  • Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
Parking
Parking
  • Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
Dining
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
Taxis
  • Available outside the terminal.
Accessibility
Accessibility
  • Elevators, ramps, toilets
WC
WC
  • Available throughout the airport.
Hotel
Hotel
  • Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
Shower
Shower
  • Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
Lounge
Lounge
  • Lounges available, including United Club and American Airlines Admirals Club.
Lost and Found Office
Lost and Found Office
  • Lost and Found located in terminal 1, near the baggage claim area.
Car Rental
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 Osceola, IA to Chicago, IL

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Trains from Osceola, IA to Chicago, IL
More information on flights to Chicago, IL

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