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Oshkosh

$111+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Feb 10 — Feb 171
Tue 2/10
Tue 2/17
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 January 11, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$111
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$254
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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Highest demand for flights based on searches. 12% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 11, 2026.

This American Airlines deal was found by Cheapflights users on 1/10. 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.
Wed 2/44:43 pmORD - ATW
Nonstop1h 08mAmerican Airlines
Sat 2/712:39 pmATW - ORD
Nonstop1h 31mAmerican Airlines
Deal found 1/10$179
This Delta deal was found by Cheapflights users on 1/9. 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.
Sun 4/121:57 pmORD - ATW
1 stop3h 45mDelta
Sun 4/194:10 pmATW - ORD
1 stop3h 38mDelta
Deal found 1/9$199
This American Airlines deal was found by Cheapflights users on 1/9. 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.
Sat 1/173:22 pmORD - ATW
Nonstop1h 11mAmerican Airlines
Wed 3/116:39 pmATW - ORD
Nonstop1h 20mAmerican Airlines
Deal found 1/9$209
This American Airlines deal was found by Cheapflights users on 1/10. 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.
Sat 10/310:00 pmORD - ATW
Nonstop1h 05mAmerican Airlines
Mon 10/56:25 pmATW - ORD
Nonstop1h 25mAmerican Airlines
Deal found 1/10$223
This Delta deal was found by Cheapflights users on 1/9. 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.
Sat 1/178:50 amORD - ATW
1 stop6h 50mDelta
Wed 3/1112:06 pmATW - ORD
1 stop5h 54mDelta
Deal found 1/9$229
This Delta deal was found by Cheapflights users on 1/10. 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.
Sat 1/248:50 amORD - ATW
1 stop6h 50mDelta
Mon 1/2612:03 pmATW - ORD
2 stops9h 02mDelta
Deal found 1/10$234
This American Airlines deal was found by Cheapflights users on 1/9. 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 1/164:43 pmORD - ATW
Nonstop1h 08mAmerican Airlines
Mon 1/197:15 amATW - ORD
Nonstop1h 32mAmerican Airlines
Deal found 1/9$239
This American Airlines deal was found by Cheapflights users on 1/10. 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.
Mon 7/2010:20 pmORD - ATW
Nonstop1h 11mAmerican Airlines
Sat 7/2510:54 amATW - ORD
Nonstop1h 18mAmerican Airlines
Deal found 1/10$241
This Delta deal was found by Cheapflights users on 1/10. 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.
Mon 1/191:58 pmORD - ATW
1 stop6h 51mDelta
Sun 1/256:10 amATW - ORD
1 stop5h 37mDelta
Deal found 1/10$244
This Delta deal was found by Cheapflights users on 1/10. 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.
Wed 1/2112:30 pmORD - ATW
2 stops8h 19mDelta
Sat 1/246:45 amATW - ORD
1 stop6h 23mDelta
Deal found 1/10$249
This Delta deal was found by Cheapflights users on 1/10. 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.
Wed 1/2112:30 pmORD - ATW
2 stops8h 19mDelta
Mon 1/2612:03 pmATW - ORD
2 stops9h 02mDelta
Deal found 1/10$254
This American Airlines deal was found by Cheapflights users on 1/10. 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.
Mon 7/2010:20 pmORD - ATW
Nonstop1h 11mAmerican Airlines
Tue 7/288:12 pmATW - ORD
Nonstop1h 23mAmerican Airlines
Deal found 1/10$255

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 January 11, 2026.
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

Sat 1/17

3:22 pm-4:33 pm

Nonstop1h 11m

Appleton Intl

Wed 3/11

6:39 pm-7:59 pm

Nonstop1h 20m

$209

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sat 1/17

8:50 am-3:40 pm

1 stop6h 50m

Appleton Intl

Wed 3/11

12:06 pm-6:00 pm

1 stop5h 54m

$229

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sat 1/24

8:50 am-3:40 pm

1 stop6h 50m

Appleton Intl

Sun 1/25

6:10 am-11:47 am

1 stop5h 37m

$229

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 1/16

4:43 pm-5:51 pm

Nonstop1h 08m

Appleton Intl

Mon 1/19

7:15 am-8:47 am

Nonstop1h 32m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sat 1/17

3:22 pm-4:33 pm

Nonstop1h 11m

Appleton Intl

Mon 1/19

6:32 pm-8:11 pm

Nonstop1h 39m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Wed 1/21

6:15 am-11:23 am

1 stop5h 08m

Appleton Intl

Sat 1/24

4:20 pm-9:43 pm

1 stop5h 23m

$244

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 1/23

6:15 am-11:23 am

1 stop5h 08m

Appleton Intl

Sun 1/25

6:10 am-11:47 am

1 stop5h 37m

$244

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Thu 1/22

8:50 am-3:40 pm

1 stop6h 50m

Appleton Intl

Sun 1/25

6:10 am-11:47 am

1 stop5h 37m

$244

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 1/23

6:15 am-11:23 am

1 stop5h 08m

Appleton Intl

Sat 1/24

4:20 pm-9:43 pm

1 stop5h 23m

$244

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Wed 1/21

12:30 pm-8:49 pm

2 stops8h 19m

Appleton Intl

Sun 1/25

6:10 am-11:47 am

1 stop5h 37m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/10

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, September is the cheapest month in which you can book a flight from Chicago to Oshkosh (average of $178). Flying from Chicago to Oshkosh in March is currently the most expensive (average of $268). 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 January 11, 2026.

It’s optimal to fly from Chicago to Oshkosh in the evening. By choosing this option you can save up to 13% on the cost of your flight, compared to a flight in the morning.

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 January 10, 2026.

Travelers seeking maximum savings on their Chicago to Oshkosh flight should consider departing on Thursday at noon when fares are most often at their lowest. Monday at noon 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 January 11, 2026.

The most flights from CHI to OS9 are scheduled on a Friday (44 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (32 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 January 11, 2026.
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
11,101 reviews

Overall

7.2

Food

6.4

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,101 reviews
American Airlines
7.2
Good
11,101 reviews

Overall

7.2

Food

6.4

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 and Delta fly from Chicago to Oshkosh in about 1h 11m. The time it takes to get you to your destination can typically vary by up to 5h 39m. 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: Republic Airways (70%), Lufthansa (64%), Air Canada( 62%).

  • What are the cheapest flights from Chicago to Oshkosh?

    Looking at all options, your cheapest flight can be booked for $98. While the most popular route (Chicago O'Hare Intl - Appleton Intl) can be booked for $179 on average, our data indicates $245 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, September is the cheapest month in which you can book a flight from Chicago to Oshkosh (average of $178). Flying from Chicago to Oshkosh in March is currently the most expensive (average of $268). 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 January 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$340FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$302FlexibilityNo cancel feeOn-time69%

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