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$122+ Cheap flights from Oshkosh, WI to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Oshkosh to Chicago

Keep the following information in mind while searching for Oshkosh to Chicago flight deals. Data was last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$227
(American Airlines)

One-way from

$122
(Mytrip)

Popular in

January

Cheapest in

May

Average price

$249
Provider with most accurate pricing for Appleton Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Appleton Intl-Chicago (CHI) flights.
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From Oshkosh to Chicago (CHI)
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One-way flight from Oshkosh to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in February 2025
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Find flight deals from Oshkosh to Chicago

Cheapest flights from Oshkosh to Chicago
Explore the most affordable flight options available from Oshkosh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/34:37 pmATW - ORD
Nonstop1h 13mAmerican Airlines
Tue 6/179:40 amORD - ATW
Nonstop1h 12mAmerican Airlines
Deal found 2/20$227
This Delta deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/115:21 pmATW - ORD
1 stop3h 24mDelta
Sat 4/196:35 amORD - ATW
1 stop4h 59mDelta
Deal found 2/19$262
This United Airlines deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/185:29 pmATW - ORD
Nonstop1h 21mUnited Airlines
Thu 5/18:05 pmORD - ATW
Nonstop1h 16mUnited Airlines
Deal found 2/20$278
This Mytrip deal was found by Cheapflights users on 2/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/181:30 pmATW - ORD
2 stops18h 10mMultiple Airlines
Thu 5/19:04 pmORD - ATW
2 stops23h 53mMultiple Airlines
Deal found 2/20$348
This Delta deal was found by Cheapflights users on 2/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/117:00 amATW - MDW
1 stop5h 35mDelta
Sat 4/193:02 pmMDW - ATW
1 stop6h 23mDelta
Deal found 2/19$353

Find flights from Oshkosh to Chicago within your budget

Customize your flight search to find flights from Oshkosh to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Oshkosh

Fly to

Chicago

Route

Depart

Return

Price

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sat 5/31

4:37 pm-5:50 pm

Nonstop1h 13m

Chicago O'Hare Intl

Sat 6/7

10:05 pm-11:05 pm

Nonstop1h 00m

$227

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sat 5/31

5:20 pm-9:04 pm

1 stop3h 44m

Chicago O'Hare Intl

Sat 6/7

6:00 am-11:12 am

1 stop5h 12m

$247

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Mon 3/17

9:00 am-7:44 am

2 stops22h 44m

Chicago O'Hare Intl

Tue 3/18

7:21 pm-11:30 pm

1 stop28h 09m

$256

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Tue 7/15

5:35 pm-6:54 pm

Nonstop1h 19m

Chicago O'Hare Intl

Thu 7/24

7:53 pm-8:58 pm

Nonstop1h 05m

$299

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Fri 4/11

7:00 am-12:35 pm

1 stop5h 35m

Chicago Midway

Sat 4/19

3:02 pm-9:25 pm

1 stop6h 23m

$353

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Sat 3/8

3:59 pm-4:36 pm

1 stop24h 37m

Chicago Midway

Mon 3/10

10:54 am-10:47 pm

2 stops35h 53m

$591

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Mon 3/10

9:00 am-7:44 am

2 stops22h 44m

$122

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Thu 3/20

4:37 pm-5:46 pm

Nonstop1h 09m

$125

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Sun 4/6

7:00 am-12:35 pm

1 stop5h 35m

$135

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Tue 3/18

12:19 pm-5:28 pm

1 stop5h 09m

$135

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 11 results
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Best time to book a flight from Oshkosh to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oshkosh with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Oshkosh to Chicago

Get recent, data-driven insights about flights from Oshkosh to Chicago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Oshkosh to Chicago?

Currently, August is the cheapest month in which you can book a flight from Oshkosh to Chicago (average of $245). Flying from Oshkosh to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OS9 to CHI?

Find hourly flight availability from Oshkosh to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 20, 2025.

When flying from Oshkosh to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Oshkosh to Chicago

Explore weekly flight availability from Oshkosh to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 20, 2025.

The most flights from OS9 to CHI are scheduled on a Tuesday (45 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (39 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated February 20, 2025.
To help decide which airline to fly from Oshkosh to Chicago, see what other customers have to say about Delta, United Airlines and Allegiant Air. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Allegiant Air
7.3
Good
765 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

Find useful and relevant information for your journey from Oshkosh to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Oshkosh to Chicago one-way?

    The cheapest airlines for a one-way flight from Oshkosh to Chicago are American Airlines ($125), Delta ($135), and United Airlines ($155).

  • What are the most reliable airlines from Oshkosh to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Oshkosh to Chicago on time: Republic Airways (95%), Qatar Airways (87%), Avianca (86%).

  • What are the cheapest flights from Oshkosh to Chicago?

    While on average a flight from Oshkosh to Chicago is generally $1,029, our data shows the cheapest flight currently is $153. When looking at the most popular route, (Appleton Intl - Chicago O'Hare Intl), you can expect to pay $227 for that flight.

  • Can I find deals for flights from Oshkosh to Chicago that include hotel bookings?

    Yes. In addition to deals on Oshkosh to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oshkosh to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oshkosh to Chicago.

  • Can I find deals for business class flights from Oshkosh to Chicago?

    Yes. Cheapflights offers flight deals from Oshkosh to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oshkosh to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Oshkosh to Chicago (average of $245). Flying from Oshkosh to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Oshkosh?

Book flights to Oshkosh if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 2 airlines flying from Oshkosh to Chicago

Discover the top 2 airlines that operate flights from Oshkosh to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$178Average$286FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$178Average$309FlexibilityNo cancel feeOn-time71%
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