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Oshkosh

$127+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$179
(American Airlines)

One-way from

$127
(Mytrip)
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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 8/298:12 amORD - ATW
Nonstop1h 05mAmerican Airlines
Sun 8/319:47 amATW - ORD
Nonstop1h 15mAmerican Airlines
Deal found 7/31$179
This United Airlines deal was found by Cheapflights users on 7/29. 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.
Tue 9/1612:55 pmORD - ATW
Nonstop1h 11mUnited Airlines
Sun 9/286:45 pmATW - ORD
Nonstop1h 25mUnited Airlines
Deal found 7/29$194
This Delta deal was found by Cheapflights users on 7/29. 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 8/295:00 pmORD - ATW
1 stop5h 17mDelta
Sun 8/317:00 amATW - ORD
1 stop3h 20mDelta
Deal found 7/29$307
This Mytrip deal was found by Cheapflights users on 7/29. 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.
Wed 8/138:12 pmORD - ATW
2 stops16h 03mMultiple Airlines
Fri 8/1510:36 amATW - ORD
3 stops33h 06mMultiple Airlines
Deal found 7/29$353

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 July 31, 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 8/29

10:25 pm-11:32 pm

Nonstop1h 07m

Appleton Intl

Sun 8/31

6:01 am-7:15 am

Nonstop1h 14m

$179

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Tue 9/16

12:55 pm-2:06 pm

Nonstop1h 11m

Appleton Intl

Sun 9/28

6:45 pm-8:10 pm

Nonstop1h 25m

$194

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 8/29

5:00 pm-10:17 pm

1 stop5h 17m

Appleton Intl

Sun 8/31

7:00 am-10:20 am

1 stop3h 20m

$307

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Wed 8/13

8:12 pm-12:15 pm

2 stops16h 03m

Appleton Intl

Fri 8/15

10:36 am-7:42 pm

3 stops33h 06m

$353

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sun 9/14

5:17 pm-10:27 am

1 stop17h 10m

$127

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sun 9/14

4:44 pm-5:47 pm

Nonstop1h 03m

$192

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Tue 9/30

7:00 am-10:40 pm

2 stops15h 40m

$199

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Wed 8/27

1:55 pm-3:09 pm

Nonstop1h 14m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 31, 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 mornings when fares are most often at their lowest. Tuesday 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 July 31, 2025.

The most flights from CHI to OS9 are scheduled on a Wednesday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (31 on average).

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 July 31, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Chicago to Oshkosh by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 cheapest airlines to fly from Chicago to Oshkosh one-way?

    The cheapest airlines for a one-way flight from Chicago to Oshkosh are Delta ($148), American Airlines ($192), and United Airlines ($280).

  • 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%), Air Canada (76%), United Airlines( 74%).

  • What are the cheapest flights from Chicago to Oshkosh?

    Looking at all options, your cheapest flight can be booked for $279. While the most popular route (Chicago O'Hare Intl - Appleton Intl) can be booked for $189 on average our data indicates $367 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$335FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$287FlexibilityNo cancel feeOn-time71%

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