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Oshkosh

$117+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
out 16 — out 231
qui 10/16
qui 10/23
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 setembro 16, 2025.

Round-trip from

$179
(American Airlines)

One-way from

$117
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$199
From Chicago (CHI) to Oshkosh
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One-way flight from Chicago (CHI) to Oshkosh
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Highest demand for flights based on searches. 11% potential increase in price ($42 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 September 2025
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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 setembro 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/14. 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.
ter 10/285:30 pmORD - ATW
Nonstop1h 02mAmerican Airlines
dom 11/27:42 pmATW - ORD
Nonstop1h 18mAmerican Airlines
Deal found 9/14$179
This American Airlines deal was found by Cheapflights users on 9/14. 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.
qui 10/28:01 amORD - ATW
Nonstop1h 05mAmerican Airlines
dom 10/59:36 amATW - ORD
Nonstop1h 15mAmerican Airlines
Deal found 9/14$184
This American Airlines deal was found by Cheapflights users on 9/15. 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.
ter 9/308:02 amORD - ATW
Nonstop1h 05mAmerican Airlines
sáb 10/46:00 amATW - ORD
Nonstop1h 17mAmerican Airlines
Deal found 9/15$189
This Delta deal was found by Cheapflights users on 9/14. 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.
sáb 10/256:08 amORD - ATW
1 stop5h 17mDelta
sáb 11/111:11 amATW - ORD
1 stop5h 00mDelta
Deal found 9/14$199
This Delta deal was found by Cheapflights users on 9/15. 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.
ter 9/306:15 amORD - ATW
1 stop5h 13mDelta
sáb 10/45:15 pmATW - ORD
1 stop4h 19mDelta
Deal found 9/15$209
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 10/307:06 pmORD - ATW
1 stop19h 19mMultiple Airlines
seg 11/34:15 pmATW - ORD
1 stop6h 24mMultiple Airlines
Deal found 9/14$219
This United Airlines deal was found by Cheapflights users on 9/14. 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.
sáb 10/251:57 pmORD - ATW
Nonstop1h 14mUnited Airlines
sáb 11/13:42 pmATW - ORD
Nonstop1h 28mUnited Airlines
Deal found 9/14$239
This American Airlines deal was found by Cheapflights users on 9/16. 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.
qua 11/198:07 amORD - ATW
Nonstop1h 09mAmerican Airlines
qui 11/279:46 amATW - ORD
Nonstop1h 17mAmerican Airlines
Deal found 9/16$240
This Delta deal was found by Cheapflights users on 9/14. 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.
sáb 10/2510:30 amORD - ATW
1 stop5h 42mDelta
qua 11/55:35 pmATW - ORD
1 stop16h 08mDelta
Deal found 9/14$242
This American Airlines deal was found by Cheapflights users on 9/16. 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.
sex 11/218:10 amORD - ATW
Nonstop1h 06mAmerican Airlines
sex 11/287:45 pmATW - ORD
Nonstop1h 18mAmerican Airlines
Deal found 9/16$247
This United Airlines deal was found by Cheapflights users on 9/15. 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.
ter 9/303:35 pmORD - ATW
Nonstop1h 14mUnited Airlines
sáb 10/45:25 pmATW - ORD
Nonstop1h 25mUnited Airlines
Deal found 9/15$249
This United Airlines deal was found by Cheapflights users on 9/14. 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.
seg 10/271:51 pmORD - ATW
Nonstop1h 16mUnited Airlines
ter 11/45:21 pmATW - ORD
Nonstop1h 29mUnited Airlines
Deal found 9/14$254

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 setembro 16, 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

ter 9/30

8:02 am-9:07 am

Nonstop1h 05m

Appleton Intl

sáb 10/4

6:00 am-7:17 am

Nonstop1h 17m

$189

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

qua 10/29

10:30 am-4:47 pm

1 stop6h 17m

Appleton Intl

sáb 11/1

11:11 am-4:11 pm

1 stop5h 00m

$199

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

ter 9/30

6:15 am-11:28 am

1 stop5h 13m

Appleton Intl

sáb 10/4

5:15 pm-9:34 pm

1 stop4h 19m

$209

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

sáb 10/25

12:52 pm-2:04 pm

Nonstop1h 12m

Appleton Intl

qui 10/30

6:21 pm-7:50 pm

Nonstop1h 29m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

sáb 10/25

12:52 pm-2:04 pm

Nonstop1h 12m

Appleton Intl

dom 11/2

2:32 pm-4:00 pm

Nonstop1h 28m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

seg 10/27

8:20 am-9:23 am

Nonstop1h 03m

Appleton Intl

qua 11/5

9:46 am-11:03 am

Nonstop1h 17m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

sáb 10/25

10:50 am-12:01 pm

Nonstop1h 11m

Appleton Intl

qua 11/5

12:38 pm-2:06 pm

Nonstop1h 28m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

seg 10/27

6:08 am-11:25 am

1 stop5h 17m

Appleton Intl

sáb 11/1

4:57 pm-8:23 pm

1 stop3h 26m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

sex 10/31

8:20 am-9:23 am

Nonstop1h 03m

Appleton Intl

sáb 11/1

6:00 am-7:16 am

Nonstop1h 16m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

qui 10/30

8:20 pm-9:33 pm

Nonstop1h 13m

Appleton Intl

qua 11/5

5:21 pm-6:50 pm

Nonstop1h 29m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 20 results
1
2

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 setembro 16, 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 setembro 16, 2025.

The most flights from CHI to OS9 are scheduled on a Monday (56 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (35 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 setembro 16, 2025.
Get a feel of what it's like to fly with 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.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Overall

7.2

Food

6.4

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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.

  • How long is the flight from Chicago to Oshkosh?

    Airlines like American Airlines, Delta, and United Airlines fly from Chicago to Oshkosh in about 1h 05m. The time it takes to get you to your destination can typically vary by up to 5h 12m. There are 160 mi between Chicago and Oshkosh. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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: Air New Zealand (72%), Qatar Airways (70%), United Airlines( 69%).

  • What are the cheapest flights from Chicago to Oshkosh?

    Looking at all options, your cheapest flight can be booked for $179. While the most popular route (Chicago O'Hare Intl - Appleton Intl) can be booked for $179 on average, our data indicates $260 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 setembro 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$276FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$184Average$327FlexibilityNo cancel feeOn-time69%

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