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Oshkosh

$124+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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 11/2510:24 pmORD - ATW
Nonstop1h 09mAmerican Airlines
Tue 12/27:42 pmATW - ORD
Nonstop1h 18mAmerican Airlines
Deal found 10/28$179
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/208:07 amORD - ATW
Nonstop1h 09mAmerican Airlines
Sun 11/239:46 amATW - ORD
Nonstop1h 17mAmerican Airlines
Deal found 10/28$180
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/128:20 pmORD - ATW
Nonstop1h 13mUnited Airlines
Sun 11/165:31 pmATW - ORD
Nonstop1h 19mUnited Airlines
Deal found 10/28$189
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/206:45 amORD - ATW
1 stop3h 43mDelta
Sun 11/237:00 amATW - ORD
1 stop6h 55mDelta
Deal found 10/28$199
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/610:45 amORD - ATW
Nonstop1h 12mUnited Airlines
Wed 11/125:31 pmATW - ORD
Nonstop1h 19mUnited Airlines
Deal found 10/28$204
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:07 amORD - ATW
Nonstop1h 09mAmerican Airlines
Sat 11/157:56 pmATW - ORD
Nonstop1h 22mAmerican Airlines
Deal found 10/29$209
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/136:45 amORD - ATW
1 stop3h 43mDelta
Sat 11/156:24 amATW - ORD
1 stop4h 00mDelta
Deal found 10/29$229
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/138:20 pmORD - ATW
Nonstop1h 13mUnited Airlines
Mon 11/178:15 amATW - ORD
Nonstop1h 28mUnited Airlines
Deal found 10/29$269
This United Airlines deal was found by Cheapflights users on 10/28. 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 10/311:42 pmORD - ATW
Nonstop1h 12mUnited Airlines
Sun 11/25:30 amATW - ORD
Nonstop1h 29mUnited Airlines
Deal found 10/28$278
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Fri 12/128:15 amORD - ATW
1 stop8h 24mMultiple Airlines
Sun 12/144:14 pmATW - ORD
2 stops24h 40mMultiple Airlines
Deal found 10/30$295

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(United Airlines)

One-way from

$124
(American Airlines)

Popular in

October

Cheapest in

June

Average price

$527
Provider with most accurate pricing for Chicago (CHI)-Appleton Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Appleton Intl flights.
Search Deals
From Chicago (CHI) to Oshkosh
Search Deals
One-way flight from Chicago (CHI) to Oshkosh
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 30, 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 12/12

8:05 am-9:08 am

Nonstop1h 03m

Appleton Intl

Sun 12/14

7:43 pm-9:14 pm

Nonstop1h 31m

$179

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Wed 11/26

3:35 pm-4:42 pm

Nonstop1h 07m

Appleton Intl

Sun 11/30

2:32 pm-4:00 pm

Nonstop1h 28m

$179

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Thu 11/20

8:07 am-9:16 am

Nonstop1h 09m

Appleton Intl

Sun 11/23

9:46 am-11:03 am

Nonstop1h 17m

$180

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Wed 11/12

8:20 pm-9:33 pm

Nonstop1h 13m

Appleton Intl

Sun 11/16

5:31 pm-6:50 pm

Nonstop1h 19m

$189

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Thu 11/20

6:45 am-10:28 am

1 stop3h 43m

Appleton Intl

Sun 11/23

7:00 am-1:55 pm

1 stop6h 55m

$199

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sat 3/28

6:00 am-11:21 am

1 stop5h 21m

Appleton Intl

Wed 4/1

11:00 am-4:37 pm

1 stop5h 37m

$199

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Thu 11/13

8:07 am-9:16 am

Nonstop1h 09m

Appleton Intl

Sat 11/15

7:56 pm-9:18 pm

Nonstop1h 22m

$209

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 12/12

10:45 am-5:14 pm

1 stop6h 29m

Appleton Intl

Sun 12/14

7:00 am-1:50 pm

1 stop6h 50m

$229

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Thu 11/13

6:45 am-10:28 am

1 stop3h 43m

Appleton Intl

Sat 11/15

6:24 am-10:24 am

1 stop4h 00m

$229

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Tue 11/25

2:23 pm-1:19 pm

1 stop22h 56m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 October 30, 2025.

It’s optimal to fly from Chicago to Oshkosh in the afternoon. By choosing this option you can save up to 20% on the cost of your flight, compared to a flight at noon.

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 Thursday at noon when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 30, 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
11,034 reviews

Crew

8.0

Comfort

7.2

Food

6.4

Entertainment

6.9

Boarding

7.5

Overall

7.2

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
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Crew

8.0

Comfort

7.2

Food

6.4

Entertainment

6.9

Boarding

7.5

Overall

7.2

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 and United Airlines fly from Chicago to Oshkosh in about 1h 03m. The time it takes to get you to your destination is usually consistent. There are 160 mi between Chicago and Oshkosh. Most flights are nonstop.

  • 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: Emirates (80%), ANA (78%), Copa Airlines( 78%).

  • 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 $179 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$282FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$301FlexibilityNo cancel feeOn-time69%

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