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Oshkosh

$113+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
1 adult, Economy
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Cheap 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 March 10, 2026.

This United Airlines deal was found by Cheapflights users on 3/8. 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 6/510:49 pm
ORD
-
ATW
Nonstop1h 26m
United Airlines
Mon 6/86:20 am
ATW
-
ORD
Nonstop1h 31m
United Airlines
Deal found 3/8$199
This American Airlines deal was found by Cheapflights users on 3/8. 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 4/224:47 pm
ORD
-
ATW
Nonstop1h 14m
American Airlines
Wed 4/296:00 am
ATW
-
ORD
Nonstop1h 29m
American Airlines
Deal found 3/8$200
This American Airlines deal was found by Cheapflights users on 3/8. 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 3/2510:15 pm
ORD
-
ATW
Nonstop1h 04m
American Airlines
Sun 3/296:39 pm
ATW
-
ORD
Nonstop1h 20m
American Airlines
Deal found 3/8$214
This Delta deal was found by Cheapflights users on 3/8. 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 6/55:19 pm
ORD
-
ATW
1 stop3h 55m
Delta
Mon 6/81:26 pm
ATW
-
ORD
1 stop5h 15m
Delta
Deal found 3/8$219
This American Airlines deal was found by Cheapflights users on 3/5. 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 3/204:49 pm
ORD
-
ATW
Nonstop1h 03m
American Airlines
Tue 3/246:39 pm
ATW
-
ORD
Nonstop1h 20m
American Airlines
Deal found 3/5$229
This Delta deal was found by Cheapflights users on 3/10. 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.
Fri 4/247:00 am
ORD
-
ATW
1 stop3h 31m
Delta
Fri 5/111:12 am
ATW
-
ORD
1 stop5h 06m
Delta
Deal found 3/10$239
This United Airlines deal was found by Cheapflights users on 3/5. 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 3/127:10 am
ORD
-
ATW
Nonstop1h 11m
United Airlines
Wed 3/2512:34 pm
ATW
-
ORD
Nonstop1h 31m
United Airlines
Deal found 3/5$244
This Delta deal was found by Cheapflights users on 3/7. 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 6/16:24 am
ORD
-
ATW
1 stop5h 27m
Delta
Sun 6/141:26 pm
ATW
-
ORD
1 stop5h 15m
Delta
Deal found 3/7$249
This United Airlines deal was found by Cheapflights users on 3/8. 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.
Sat 4/2512:50 pm
ORD
-
ATW
Nonstop1h 10m
United Airlines
Wed 4/2910:30 am
ATW
-
ORD
Nonstop1h 26m
United Airlines
Deal found 3/8$259
This United Airlines deal was found by Cheapflights users on 3/5. 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 3/207:10 am
ORD
-
ATW
Nonstop1h 11m
United Airlines
Tue 3/245:23 pm
ATW
-
ORD
Nonstop1h 26m
United Airlines
Deal found 3/5$289

Find flight deals from Chicago to Oshkosh

Keep the following information in mind while searching for Chicago to Oshkosh flight deals. Data was last updated March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$199
(United Airlines)

One-way from

$113
(Kiwi.com)

Popular in

October

Cheapest in

June

Average price

$325
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 ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 10, 2026.
Use the filters below to find and compare flights from Chicago to Oshkosh that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Mon 6/1

7:50 pm-9:21 pm

Nonstop1h 31m

Appleton Intl

Sun 6/14

8:00 am-9:30 am

Nonstop1h 30m

$199

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Wed 3/25

10:15 pm-11:19 pm

Nonstop1h 04m

Appleton Intl

Sun 3/29

6:39 pm-7:59 pm

Nonstop1h 20m

$214

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Thu 8/20

8:55 am-12:46 pm

1 stop3h 51m

Appleton Intl

Tue 8/25

10:55 am-4:36 pm

1 stop5h 41m

$219
Quickest round-trip

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 3/20

4:49 pm-5:52 pm

Nonstop1h 03m

Appleton Intl

Tue 3/24

6:39 pm-7:59 pm

Nonstop1h 20m

$229

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 7/17

8:55 am-12:46 pm

1 stop3h 51m

Appleton Intl

Sun 7/19

1:26 pm-6:41 pm

1 stop5h 15m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 4/24

7:00 am-10:31 am

1 stop3h 31m

Appleton Intl

Fri 5/1

11:12 am-4:18 pm

1 stop5h 06m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Mon 6/1

6:24 am-11:51 am

1 stop5h 27m

Appleton Intl

Sun 6/14

1:26 pm-6:41 pm

1 stop5h 15m

$249

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sat 4/25

1:55 pm-3:11 pm

Nonstop1h 16m

Appleton Intl

Wed 4/29

3:46 pm-5:05 pm

Nonstop1h 19m

$259
Cheapest one-way

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Thu 5/7

6:24 am-11:51 am

1 stop5h 27m

$154
Quickest one-way

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Mon 5/4

5:04 pm-8:37 pm

1 stop3h 33m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

Showing 1-10 of 17 resultsSorted by cheapest first
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 $373). 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 March 10, 2026.

It’s optimal to fly from Chicago to Oshkosh in the morning. By choosing this option you can save up to 12% on the cost of your flight, compared to a flight in the afternoon.

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 February 21, 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 March 10, 2026.

The most flights from CHI to OS9 are scheduled on a Monday (58 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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 March 10, 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
7.1
Good
11,414 reviews

Overall

7.1

Boarding

7.5

Crew

7.9

Food

6.4

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,414 reviews
American Airlines
7.1
Good
11,414 reviews

Overall

7.1

Boarding

7.5

Crew

7.9

Food

6.4

Comfort

7.2

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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 United Airlines, American Airlines, and Delta fly from Chicago to Oshkosh in about 1h 04m. The time it takes to get you to your destination can typically vary by up to 2h 47m. 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 (100%), PSA Airlines (94%), Lufthansa( 73%).

  • What are the cheapest flights from Chicago to Oshkosh?

    Looking at all options, your cheapest flight can be booked for $58. While the most popular route (Chicago O'Hare Intl - Appleton Intl) can be booked for $199 on average, our data indicates $118 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 $373). 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

Browse thousands of different options on Cheapflights for your next trip

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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 March 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$258FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$359FlexibilityNo cancel feeOn-time69%

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