1,000+ travel companies
1,000+ travel companies
Scan to get our free app
Use our app to get live travel updates and book mobile tickets for trains, buses, flights, and ferries.
App Store
4.942K ratings
Google Play
4.6136K reviews
Journey information
Overview: Osceola, IA to Chicago, IL flight
USAUSA
Flights from Osceola, IA to Chicago, IL depart on average 24 times per day, taking around 1h 49m. Cheap flight tickets for this journey start at $230 (€182) but you can travel from only $53 (€42) by train.
There are 3 flights per day. The earliest flight runs at 05:00, the last at 22:40. The fastest flight covers the 321 miles (518 km) distance in 1h 23m. March 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 $53 (€42)
Distance 321 miles (518 km) |
Average flight duration 1h 49m |
Cheapest ticket price $230 (€182) |
Flights per day 24 |
Direct flights 3 |
Fastest flight 1h 23m |
Cheapest month to travel March |
First flight 05:00 |
Last flight 22:40 |
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 $53 (€42)
The cheapest and fastest flights from Osceola, IA to Chicago, IL
Showing times and prices for Feb 01
Cheapest price
$268
Average price
$891
Fastest journey
1 h 33 m
Average duration
1 h 36 m
Flights per day
59
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 $891 if you buy it on the day, but the cheapest tickets can be found for only $268.
Fast flights
Of the 59 flights that leave Osceola, IA for Chicago, IL onSun, Feb 01, 8 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sun, Feb 01 the direct flights cover the 518 km distance in an average of 1 h 36 m but if you time it right, some flights will get you there in just 1 h 33 m .
On Sun, Feb 01 the longest flights will take 1 h 38 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.
AA499605:01PM1h47
Des Moines International Airport06:48PMO'Hare International Airport
$2681One-way
0 transfers
AA342106:07AM1h42
Des Moines International Airport07:49AMO'Hare International Airport
$2681One-way
0 transfers
AA413607:10AM1h44
Des Moines International Airport08:54AMO'Hare International Airport
$2681One-way
0 transfers
AA2488 · AA219907:40AM8h00
Des Moines International Airport03:40PMO'Hare International Airport
$2811One-way
1 transfer
AA2488 · AA223607:40AM5h42
Des Moines International Airport01:22PMO'Hare International Airport
$2811One-way
1 transfer
UA521906:48PM1h33
Des Moines International Airport08:21PMO'Hare International Airport
$3081One-way
0 transfers
UA31203:35PM1h35
Des Moines International Airport05:10PMO'Hare International Airport
$3081One-way
0 transfers
AA346911:42AM1h36
Des Moines International Airport01:18PMO'Hare International Airport
$4131One-way
0 transfers
UA418211:30AM1h37
Des Moines International Airport01:07PMO'Hare International Airport
$3081One-way
0 transfers
UA136308:00AM1h38
Des Moines International Airport09:38AMO'Hare International Airport
$3081One-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 €42. For those with little time consider booking a flight which can get you there in 1h 49m. The ticket price range depends on the travel mode: a train costs an average of €42, and a flight costs an average of €182.
Distance: 321 miles (518 km)
Compare flight with
| Flight | Most popular Train |
|---|---|
€244 Average price | €70 Average price Cheapest |
4h 49m Average total duration Fastest 1h 49m Onboard + 3h 0m Additional time* | 7h 35m Average total duration 7h 5m Onboard + 30m Additional time* |
Direct Options | Direct Options |
Live departures
Osceola, IA to Chicago, IL flight times
The table below shows live departures for Osceola, IA to Chicago, IL flights for today, Saturday, January 31. You can also manually refresh the results below to see updated flight journeys.
Last updated at 4:17 AM
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| AA941 · AA1417 | 11:25 AM Des Moines International Airport | 8h51 | 8:16 PM O'Hare International Airport | 1 transfer | |
| UA4777 · UA617 | 11:30 AM Des Moines International Airport | 11h34 | 11:04 PM O'Hare International Airport | 1 transfer | |
| UA4777 · UA1023 | 11:30 AM Des Moines International Airport | 13h16 | 12:46 AM O'Hare International Airport | 1 transfer | |
| UA4777 · UA2865 | 11:30 AM Des Moines International Airport | 9h25 | 8:55 PM O'Hare International Airport | 1 transfer | |
| UA4777 · UA2329 | 11:30 AM Des Moines International Airport | 7h52 | 7:22 PM O'Hare International Airport | 1 transfer | |
| UA4777 · UA1411 | 11:30 AM Des Moines International Airport | 15h45 | 3:15 AM O'Hare International Airport | 1 transfer | |
| UA4777 · UA2430 | 11:30 AM Des Moines International Airport | 6h04 | 5:34 PM O'Hare International Airport | 1 transfer | |
 AA4698 · AA4731 | 12:00 PM Des Moines International Airport | 9h13 | 9:13 PM O'Hare International Airport | 1 transfer | |
| AA4698+AA3296 | 12:00 PM Des Moines International Airport | 16h34 | 4:34 AM O'Hare International Airport | 1 transfer | |
| AA4698 · AA4635 | 12:00 PM Des Moines International Airport | 13h29 | 1:29 AM O'Hare International Airport | 1 transfer | |
| AA4698+AA1944 | 12:00 PM Des Moines International Airport | 7h16 | 7:16 PM O'Hare International Airport | 1 transfer | |
| AA4698+AA2152 | 12:00 PM Des Moines International Airport | 10h50 | 10:50 PM O'Hare International Airport | 1 transfer | |
| UA3047 | 12:30 PM Des Moines International Airport | 1h38 | 2:08 PM O'Hare International Airport | 0 transfersDirect | |
| AA2488 · AA1199 | 1:40 PM Des Moines International Airport | 12h10 | 1:50 AM O'Hare International Airport | 1 transfer | |
| AA2488 · AA2199 | 1:40 PM Des Moines International Airport | 8h00 | 9:40 PM O'Hare International Airport | 1 transfer | |
| AA2488 · AA2236 | 1:40 PM Des Moines International Airport | 5h42 | 7:22 PM O'Hare International Airport | 1 transfer | |
| AA2488 · AA1039 | 1:40 PM Des Moines International Airport | 15h47 | 5:27 AM O'Hare International Airport | 1 transfer | |
| AA2488 · AA2298 | 1:40 PM Des Moines International Airport | 10h21 | 12:01 AM O'Hare International Airport | 1 transfer | |
| UA1363 | 1:50 PM Des Moines International Airport | 1h38 | 3:28 PM O'Hare International Airport | 0 transfersDirect | |
| UA1982 · UA1528 | 2:10 PM Des Moines International Airport | 6h30 | 8:40 PM O'Hare International Airport | 1 transfer | |
| UA1982 · UA787 | 2:10 PM Des Moines International Airport | 11h40 | 1:50 AM O'Hare International Airport | 1 transfer | |
| UA1982 · UA1608 | 2:10 PM Des Moines International Airport | 8h56 | 11:06 PM O'Hare International Airport | 1 transfer | |
| UA1982 · UA1293 | 2:10 PM Des Moines International Airport | 16h18 | 6:28 AM O'Hare International Airport | 1 transfer | |
| UA1982 · UA2197 | 2:10 PM Des Moines International Airport | 13h16 | 3:26 AM O'Hare International Airport | 1 transfer | |
| AA3469 | 5:42 PM Des Moines International Airport | 1h36 | 7:18 PM O'Hare International Airport | 0 transfersDirect | |
| AA4806 · AA4635 | 7:16 PM Des Moines International Airport | 6h13 | 1:29 AM O'Hare International Airport | 1 transfer | |
| AA4806+AA3296 | 7:16 PM Des Moines International Airport | 9h18 | 4:34 AM O'Hare International Airport | 1 transfer | |
| UA4798 · UA377 | 7:35 PM Des Moines International Airport | 10h24 | 5:59 AM O'Hare International Airport | 1 transfer | |
| UA4798 · UA1411 | 7:35 PM Des Moines International Airport | 7h40 | 3:15 AM O'Hare International Airport | 1 transfer | |
| UA6117 · UA1488 | 9:04 PM Des Moines International Airport | 16h43 | 1:47 PM O'Hare International Airport | 1 transfer | |
| UA6117 · UA2197 | 9:04 PM Des Moines International Airport | 6h22 | 3:26 AM O'Hare International Airport | 1 transfer | |
| UA6117 · UA2616 | 9:04 PM Des Moines International Airport | 18h04 | 3:08 PM O'Hare International Airport | 1 transfer | |
| UA6117 · UA1293 | 9:04 PM Des Moines International Airport | 9h24 | 6:28 AM O'Hare International Airport | 1 transfer | |
| UA312 | 9:35 PM Des Moines International Airport | 1h35 | 11:10 PM O'Hare International Airport | 0 transfersDirect | |
| AA2970 · AA395 | 10:00 PM Des Moines International Airport | 15h21 | 1:21 PM O'Hare International Airport | 1 transfer | |
| AA2970 · AA1573 | 10:00 PM Des Moines International Airport | 7h44 | 5:44 AM O'Hare International Airport | 1 transfer | |
| AA2970 · AA779 | 10:00 PM Des Moines International Airport | 6h18 | 4:18 AM O'Hare International Airport | 1 transfer | |
| AA2970+AA3389 | 10:00 PM Des Moines International Airport | 5h27 | 3:27 AM O'Hare International Airport | 1 transfer | |
 AA5474+AA1039 | 11:00 PM Des Moines International Airport | 6h27 | 5:27 AM O'Hare International Airport | 1 transfer | |
| AA5474+AA1409 | 11:00 PM Des Moines International Airport | 16h05 | 3:05 PM O'Hare International Airport | 1 transfer | |
| AA4996 | 11:01 PM Des Moines International Airport | 1h47 | 12:48 AM O'Hare International Airport | 0 transfersDirect | |
| UA4662 · UA377 | 11:09 PM Des Moines International Airport | 6h50 | 5:59 AM O'Hare International Airport | 1 transfer | |
| UA4662 · UA1377 | 11:09 PM Des Moines International Airport | 16h35 | 3:44 PM O'Hare International Airport | 1 transfer | |
| UA4662 · UA2430 | 11:09 PM Des Moines International Airport | 18h25 | 5:34 PM O'Hare International Airport | 1 transfer | |
| AA3191 · AA395 | 11:51 PM Des Moines International Airport | 13h30 | 1:21 PM O'Hare International Airport | 1 transfer | |
| AA3191 · AA1315 | 11:51 PM Des Moines International Airport | 14h47 | 2:38 PM O'Hare International Airport | 1 transfer | |
| AA3191 · AA2999 | 11:51 PM Des Moines International Airport | 16h02 | 3:53 PM O'Hare International Airport | 1 transfer | |
| AA3191 · AA1573 | 11:51 PM Des Moines International Airport | 5h53 | 5:44 AM O'Hare International Airport | 1 transfer | |
| Sunday, February 1 | |||||
| UA5219 | 12:48 AM Des Moines International Airport | 1h33 | 2:21 AM O'Hare International Airport | 0 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.
Sun
Feb 01
Feb 01
Mon
Feb 02
Feb 02
Tue
Feb 03
Feb 03
Wed
Feb 04
Feb 04
Thu
Feb 05
Feb 05
Fri
Feb 06
Feb 06
Sat
Feb 07
Feb 07
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.
Cheap plane tickets from Osceola, IA to Chicago, IL can start from as little as $230 (€182) when you book in advance. The average flight ticket price for Osceola, IA to Chicago, IL is $309 (€244) ; 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 23m 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 10:40 PM.
The cheapest month for a flight from Osceola, IA to Chicago, IL is March.
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.
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 season to visit Chicago, IL is 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 Osceola, IA to Chicago, IL
Osceola
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 Osceola, IA to Chicago, IL
Here are some other resources that might have the information you need
Most popular flights to and from Chicago, IL and Osceola, IA
The Omio App Makes Travel Planning Easy
We’ll get you where you want to go. From live train updates to mobile tickets, our innovative app is the ideal way to plan and keep track of your travel.
