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Oshkosh

$157+ Cheap flights from Chicago (CHI) to Oshkosh, WI

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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
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Cheap flight deals from Chicago to Oshkosh

Keep the following information in mind while searching for Chicago to Oshkosh flight deals. Data was last updated April 22, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$157
(American Airlines)
Provider with most accurate pricing for Chicago (CHI)-Appleton Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Appleton Intl flights.
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From Chicago (CHI) to Oshkosh
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One-way flight from Chicago (CHI) to Oshkosh
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Find flight deals from Chicago to Oshkosh

Cheapest flights from Chicago to Oshkosh
Explore the most affordable flight options available from Chicago to Oshkosh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

This United Airlines deal was found by Cheapflights users on 4/21. 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 6/205:57 pmORD - ATW
Nonstop1h 13mUnited Airlines
Tue 7/151:05 pmATW - ORD
Nonstop1h 21mUnited Airlines
Deal found 4/21$179
This American Airlines deal was found by Cheapflights users on 4/21. 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 5/279:50 amORD - ATW
Nonstop1h 06mAmerican Airlines
Sat 8/166:19 amATW - ORD
Nonstop1h 11mAmerican Airlines
Deal found 4/21$180
This Delta deal was found by Cheapflights users on 4/22. 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.
Tue 5/2711:03 amORD - ATW
1 stop4h 37mDelta
Sat 8/165:20 pmATW - ORD
1 stop3h 44mDelta
Deal found 4/22$199
This Mytrip deal was found by Cheapflights users on 4/20. 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.
Sun 7/205:42 pmORD - ATW
1 stop29h 24mMultiple Airlines
Thu 7/247:00 amATW - ORD
1 stop16h 10mMultiple Airlines
Deal found 4/20$409

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Oshkosh 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 April 22, 2025.
Use the filters below to find and compare flights from Chicago to Oshkosh that are best for you.

Fly from

Chicago

Fly to

Oshkosh

Route

Depart

Return

Price

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 6/20

5:57 pm-7:10 pm

Nonstop1h 13m

Appleton Intl

Tue 7/15

1:05 pm-2:26 pm

Nonstop1h 21m

$179

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Tue 5/27

9:50 am-10:56 am

Nonstop1h 06m

Appleton Intl

Sat 8/16

6:19 am-7:30 am

Nonstop1h 11m

$180

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Tue 5/27

11:03 am-3:40 pm

1 stop4h 37m

Appleton Intl

Sat 8/16

5:20 pm-9:04 pm

1 stop3h 44m

$199

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sun 7/20

5:42 pm-11:06 pm

1 stop29h 24m

Appleton Intl

Thu 7/24

7:00 am-11:10 pm

1 stop16h 10m

$409

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sun 5/4

9:46 am-10:54 am

Nonstop1h 08m

$157

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sun 5/4

6:45 am-10:24 am

1 stop3h 39m

$167

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 6/20

5:50 pm-10:11 pm

2 stops28h 21m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Best time to book a flight from Chicago to Oshkosh

Have a flexible travel schedule? Discover the best time to fly to Oshkosh from Chicago 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Oshkosh

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Oshkosh (average of $280). Flying from Chicago to Oshkosh in June is currently the most expensive (average of $376). 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 CHI to OS9?

Find hourly flight availability from Chicago to Oshkosh. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 22, 2025.

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

What is the cheapest day to fly from Chicago to Oshkosh?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Oshkosh. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Oshkosh flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Oshkosh

Explore weekly flight availability from Chicago to Oshkosh. 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 April 22, 2025.

The most flights from CHI to OS9 are scheduled on a Tuesday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 on average).

Rainfall in Oshkosh by month

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

In terms of precipitation, rainfall in Oshkosh ranges from 1.1 - 3.8 inches per month. June is typically the wettest month, when rainfall can reach 3.8 in. February is typically the driest time to visit Oshkosh when rainfall is around 1.1 in.

Temperature in Oshkosh by month

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

If weather is an important factor for your trip to Oshkosh, 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 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 17.6 F).

Reviews of airlines servicing Oshkosh

Get insights into the airlines that provide service to Oshkosh. 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 Oshkosh. Reviews last updated April 22, 2025.
Read through reviews of airlines operating flights from Chicago to Oshkosh, such as Delta, United Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

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
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

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
8,683 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

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
7,920 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

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 Chicago to Oshkosh. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Before booking your flight to Oshkosh from Chicago, check out the most reliable airlines to get you to your destination on time: Republic Airways (100%), Aer Lingus (78%), SkyWest Airlines( 72%).

  • What are the cheapest flights from Chicago to Oshkosh?

    Looking at all options, your cheapest flight can be booked for $119. While the most popular route (Chicago O'Hare Intl - Appleton Intl) can be booked for $179 on average our data indicates $281 when flying from Chicago to Oshkosh.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Oshkosh 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 Chicago to Oshkosh?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Oshkosh (average of $280). Flying from Chicago to Oshkosh in June is currently the most expensive (average of $376). 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

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Alternative routes for Chicago to Oshkosh

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Top 2 airlines flying from Chicago to Oshkosh

Discover the top 2 airlines that operate flights from Chicago to Oshkosh. 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$169Average$317FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$184Average$357FlexibilityNo cancel feeOn-time71%

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