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Oshkosh

$100+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MKE
May 30 — Jun 61
Sat 5/30
Sat 6/6
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 April 30, 2026.

This American Airlines deal was found by Cheapflights users on 4/28. 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 5/264:51 pm
ORD
-
ATW
Nonstop1h 18m
American Airlines
Tue 6/26:41 pm
ATW
-
ORD
Nonstop1h 37m
American Airlines
Deal found 4/28$239
This American Airlines deal was found by Cheapflights users on 4/27. 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 6/119:30 am
ORD
-
ATW
Nonstop1h 16m
American Airlines
Thu 6/186:28 pm
ATW
-
ORD
Nonstop1h 35m
American Airlines
Deal found 4/27$241
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Wed 6/175:10 am
ORD
-
ATW
1 stop8h 23m
American Airlines
Wed 9/306:26 pm
ATW
-
ORD
Nonstop1h 24m
American Airlines
Deal found 4/28$251
This American Airlines deal was found by Cheapflights users on 4/27. 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 5/1410:32 pm
ORD
-
ATW
Nonstop1h 08m
American Airlines
Wed 5/206:30 pm
ATW
-
ORD
Nonstop1h 32m
American Airlines
Deal found 4/27$254
This Delta deal was found by Cheapflights users on 4/28. 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.
Tue 5/267:00 am
ORD
-
ATW
1 stop3h 28m
Delta
Tue 6/24:13 pm
ATW
-
ORD
1 stop5h 07m
Delta
Deal found 4/28$259
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Fri 5/158:55 am
ORD
-
ATW
Nonstop1h 10m
American Airlines
Sun 5/175:40 am
ATW
-
ORD
Nonstop1h 27m
American Airlines
Deal found 4/29$269
This Kiwi.com deal was found by Cheapflights users on 4/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/219:37 pm
ORD
-
ATW
1 stop25h 42m
Multiple Airlines
Sun 5/242:44 pm
ATW
-
ORD
2 stops41h 11m
Multiple Airlines
Deal found 4/28$276
This United Airlines deal was found by Cheapflights users on 4/27. 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 5/712:49 pm
ORD
-
ATW
Nonstop1h 12m
United Airlines
Wed 5/132:43 pm
ATW
-
ORD
Nonstop1h 26m
United Airlines
Deal found 4/27$284
This Delta deal was found by Cheapflights users on 4/27. 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.
Tue 5/127:00 am
ORD
-
ATW
1 stop3h 28m
Delta
Sat 5/164:13 pm
ATW
-
ORD
1 stop5h 07m
Delta
Deal found 4/27$289
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
Thu 5/145:30 pm
ORD
-
ATW
1 stop20h 12m
Multiple Airlines
Sun 5/176:30 am
ATW
-
ORD
1 stop25h 52m
Multiple Airlines
Deal found 4/25$296
This Delta deal was found by Cheapflights users on 4/28. 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 5/72:00 pm
ORD
-
ATW
1 stop3h 34m
Delta
Wed 5/134:13 pm
ATW
-
ORD
1 stop5h 07m
Delta
Deal found 4/28$304
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Sun 6/148:45 am
ORD
-
ATW
Nonstop1h 18m
United Airlines
Thu 9/105:27 pm
ATW
-
ORD
Nonstop1h 29m
United Airlines
Deal found 4/27$308

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 April 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(American Airlines)

One-way from

$100
(Kiwi.com)

Popular in

October

Cheapest in

June
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. 18% potential increase in price ($61 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($21 potential savings vs. average RT price).
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 April 30, 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

Sat 7/25

5:55 pm-7:16 pm

Nonstop1h 21m

Appleton Intl

Sun 7/26

8:13 pm-9:45 pm

Nonstop1h 32m

$239

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Tue 5/26

7:00 am-10:28 am

1 stop3h 28m

Appleton Intl

Tue 6/2

4:13 pm-9:20 pm

1 stop5h 07m

$259

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sat 5/23

7:00 am-10:28 am

1 stop3h 28m

Appleton Intl

Fri 5/29

4:13 pm-9:20 pm

1 stop5h 07m

$259

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 6/12

6:30 am-10:47 am

1 stop4h 17m

Appleton Intl

Sun 6/14

2:07 pm-6:29 pm

1 stop4h 22m

$259

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sun 6/14

6:30 am-10:47 am

1 stop4h 17m

Appleton Intl

Sun 6/21

2:07 pm-6:29 pm

1 stop4h 22m

$289

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Thu 5/21

7:00 am-10:28 am

1 stop3h 28m

Appleton Intl

Sun 5/24

4:13 pm-9:20 pm

1 stop5h 07m

$289

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Fri 7/17

7:05 am-1:23 pm

1 stop6h 18m

Appleton Intl

Sun 7/19

2:03 pm-6:29 pm

1 stop4h 26m

$289

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Sun 6/14

9:22 pm-10:45 pm

Nonstop1h 23m

Appleton Intl

Thu 9/10

3:47 pm-5:16 pm

Nonstop1h 29m

$309
Quickest round-trip

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Thu 5/21

8:45 am-10:03 am

Nonstop1h 18m

Appleton Intl

Sun 5/24

12:30 pm-1:53 pm

Nonstop1h 23m

$310

ChicagoAppleton

ORD - ATW

ORDATW

Chicago O'Hare Intl

Wed 6/17

6:30 am-10:47 am

1 stop4h 17m

Appleton Intl

Wed 9/30

10:55 am-4:36 pm

1 stop5h 41m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 19 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 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 April 30, 2026.

It’s optimal to fly from Chicago to Oshkosh at noon. By choosing this option you can save up to 6% on the cost of your flight, compared to a flight in the evening.

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 April 25, 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 evenings 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 April 30, 2026.

The most flights from CHI to OS9 are scheduled on a Wednesday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 on average).

How much does it cost to fly round-trip from Chicago to Oshkosh?

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 18m. The time it takes to get you to your destination can typically vary by up to 2h 10m. 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: Envoy Air (75%), Lufthansa (70%), PSA Airlines( 62%).

  • What are the cheapest flights from Chicago to Oshkosh?

    Looking at all options, your cheapest flight can be booked for $85. While the most popular route (Chicago O'Hare Intl - Appleton Intl) can be booked for $239 on average, our data indicates $223 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 April 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$254FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$389FlexibilityNo cancel feeOn-time69%

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