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$121+ Cheap flights from Oshkosh, WI to Chicago (CHI)

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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap flight deals from Oshkosh to Chicago

Keep the following information in mind while searching for Oshkosh to Chicago flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$179
(American Airlines)

One-way from

$121
(Kiwi.com)

Popular in

January

Cheapest in

July

Average price

$346
From Oshkosh to Chicago (CHI)
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One-way flight from Oshkosh to Chicago (CHI)
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Highest demand for flights based on searches. 14% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($17 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 Oshkosh to Chicago

Cheapest flights from Oshkosh to Chicago
Explore the most affordable flight options available from Oshkosh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 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.
sáb. 10/119:53 amATW - ORD
Nonstop1h 15mAmerican Airlines
dom. 10/128:20 amORD - ATW
Nonstop1h 03mAmerican Airlines
Deal found 9/14$179
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.
jue. 10/96:13 pmATW - ORD
Nonstop1h 25mAmerican Airlines
dom. 10/128:20 amORD - ATW
Nonstop1h 03mAmerican Airlines
Deal found 9/16$180
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.
mar. 9/306:18 pmATW - ORD
Nonstop1h 25mAmerican Airlines
mar. 10/148:20 amORD - ATW
Nonstop1h 03mAmerican Airlines
Deal found 9/14$184
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/35:20 pmATW - ORD
Nonstop1h 29mUnited Airlines
dom. 12/712:45 pmORD - ATW
Nonstop1h 12mUnited Airlines
Deal found 9/16$188
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.
mar. 9/306:18 pmATW - ORD
Nonstop1h 25mAmerican Airlines
sáb. 10/48:02 amORD - ATW
Nonstop1h 05mAmerican Airlines
Deal found 9/15$189
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.
jue. 9/256:19 pmATW - ORD
Nonstop1h 25mAmerican Airlines
dom. 10/58:01 amORD - ATW
Nonstop1h 05mAmerican Airlines
Deal found 9/14$194
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.
sáb. 10/412:37 pmATW - ORD
Nonstop1h 24mUnited Airlines
sáb. 10/118:10 pmORD - ATW
Nonstop1h 23mUnited Airlines
Deal found 9/15$198
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.
sáb. 10/1111:11 amATW - ORD
1 stop5h 00mDelta
jue. 10/166:08 amORD - ATW
1 stop5h 17mDelta
Deal found 9/15$199
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/307:00 amATW - ORD
1 stop3h 19mDelta
mar. 10/146:08 amORD - ATW
1 stop5h 17mDelta
Deal found 9/16$204
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.
vie. 11/75:21 pmATW - ORD
Nonstop1h 29mUnited Airlines
dom. 11/98:20 pmORD - ATW
Nonstop1h 13mUnited Airlines
Deal found 9/14$207
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.
mar. 9/304:16 pmATW - ORD
1 stop5h 05mDelta
mar. 10/76:08 amORD - ATW
1 stop5h 17mDelta
Deal found 9/15$214
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.
mar. 9/304:16 pmATW - ORD
1 stop5h 05mDelta
sáb. 10/47:10 amORD - ATW
1 stop3h 18mDelta
Deal found 9/15$219

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oshkosh to Chicago 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 septiembre 16, 2025.
Use the filters below to find and compare flights from Oshkosh to Chicago that are best for you.

Fly from

Oshkosh

Fly to

Chicago

Route

Depart

Return

Price

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

sáb. 10/11

9:53 am-11:08 am

Nonstop1h 15m

Chicago O'Hare Intl

dom. 10/12

8:20 am-9:23 am

Nonstop1h 03m

$179

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

dom. 12/21

5:23 pm-6:55 pm

Nonstop1h 32m

Chicago O'Hare Intl

dom. 12/28

6:05 pm-7:19 pm

Nonstop1h 14m

$179

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

jue. 10/2

6:19 pm-7:44 pm

Nonstop1h 25m

Chicago O'Hare Intl

jue. 10/16

8:20 am-9:23 am

Nonstop1h 03m

$184

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

mié. 12/3

5:20 pm-6:49 pm

Nonstop1h 29m

Chicago O'Hare Intl

dom. 12/7

12:45 pm-1:57 pm

Nonstop1h 12m

$188

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

sáb. 2/28

12:06 pm-6:08 pm

1 stop6h 02m

Chicago Midway

mié. 3/4

1:00 pm-4:42 pm

1 stop3h 42m

$199

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

sáb. 10/11

11:11 am-4:11 pm

1 stop5h 00m

Chicago O'Hare Intl

sáb. 10/18

7:10 am-10:31 am

1 stop3h 21m

$199

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

sáb. 2/28

12:06 pm-4:48 pm

1 stop4h 42m

Chicago O'Hare Intl

mié. 3/4

6:00 am-11:21 am

1 stop5h 21m

$199

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

mar. 9/30

4:16 pm-9:21 pm

1 stop5h 05m

Chicago O'Hare Intl

mar. 10/14

7:10 am-10:31 am

1 stop3h 21m

$204

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

vie. 11/7

5:21 pm-6:50 pm

Nonstop1h 29m

Chicago O'Hare Intl

dom. 11/9

8:20 pm-9:33 pm

Nonstop1h 13m

$207

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

mar. 9/30

4:16 pm-9:21 pm

1 stop5h 05m

Chicago O'Hare Intl

sáb. 10/4

7:10 am-10:28 am

1 stop3h 18m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 28 results
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Best time to book a flight from Oshkosh to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Oshkosh 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 Oshkosh to Chicago

What is the cheapest month to book a flight from Oshkosh to Chicago?

Currently, August is the cheapest month in which you can book a flight from Oshkosh to Chicago (average of $245). Flying from Oshkosh to Chicago in March is currently the most expensive (average of $321). 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 OS9 to CHI?

Find hourly flight availability from Oshkosh to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

When flying from Oshkosh to Chicago, 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 Oshkosh to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Oshkosh to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oshkosh to Chicago flight should consider departing on Wednesday afternoons 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 Oshkosh to Chicago

Explore weekly flight availability from Oshkosh to Chicago. 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 septiembre 16, 2025.

The most flights from OS9 to CHI are scheduled on a Monday (54 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (31 on average).

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

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated septiembre 16, 2025.
Read through reviews of airlines operating flights from Oshkosh to Chicago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,924 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Overall

7.4

Crew

8.1

Boarding

7.7

Comfort

7.3

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Oshkosh to Chicago. 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 Oshkosh to Chicago?

    A quick flight from Oshkosh to Chicago can take about 1h 15m. American Airlines provides one of the quickest options available for as low as $179. The distance between Oshkosh and Chicago is about 160 mi. This flight may include one or multiple stops.

  • What are the most reliable airlines from Oshkosh to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Oshkosh to Chicago on time: Copa Airlines (72%), Alaska Airlines (71%), Avianca (71%).

  • What are the cheapest flights from Oshkosh to Chicago?

    While on average a flight from Oshkosh to Chicago is generally $932, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Appleton Intl - Chicago O'Hare Intl), you can expect to pay $179 for that flight.

  • Can I find deals for flights from Oshkosh to Chicago that include hotel bookings?

    Yes. In addition to deals on Oshkosh to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oshkosh to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oshkosh to Chicago.

  • Can I find deals for business class flights from Oshkosh to Chicago?

    Yes. Cheapflights offers flight deals from Oshkosh to Chicago 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 Oshkosh to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Oshkosh to Chicago (average of $245). Flying from Oshkosh to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Oshkosh to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Oshkosh to Chicago

Discover the top 2 airlines that operate flights from Oshkosh to Chicago. 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$302FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$288FlexibilityNo cancel feeOn-time71%

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