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$131+ 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 6/23. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$179
(American Airlines)

One-way from

$131
(Mytrip)

Popular in

January

Cheapest in

July

Average price

$212
From Oshkosh to Chicago (CHI)
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One-way flight from Oshkosh to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($50 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 June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/12. 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 9/256:19 pmATW - ORD
Nonstop1h 25mAmerican Airlines
Sun 10/510:30 pmORD - ATW
Nonstop1h 07mAmerican Airlines
Deal found 6/12$179
This Delta deal was found by Cheapflights users on 6/11. 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 7/211:59 amATW - MDW
1 stop5h 41mDelta
Wed 7/99:24 amMDW - ATW
1 stop6h 06mDelta
Deal found 6/11$199
This Delta deal was found by Cheapflights users on 6/11. 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 6/274:14 pmATW - ORD
1 stop5h 23mDelta
Wed 7/911:05 amORD - ATW
1 stop4h 25mDelta
Deal found 6/11$204
This United Airlines deal was found by Cheapflights users on 6/11. 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 6/272:43 pmATW - ORD
Nonstop1h 20mUnited Airlines
Tue 7/18:20 pmORD - ATW
Nonstop1h 15mUnited Airlines
Deal found 6/11$225
This Mytrip deal was found by Cheapflights users on 6/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/119:02 amATW - ORD
1 stop12h 28mMultiple Airlines
Fri 7/183:18 pmORD - ATW
1 stop31h 01mMultiple Airlines
Deal found 6/12$230

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 June 12, 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

Thu 9/25

6:19 pm-7:44 pm

Nonstop1h 25m

Chicago O'Hare Intl

Sun 10/5

10:30 pm-11:37 pm

Nonstop1h 07m

$179

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Wed 7/2

11:59 am-5:40 pm

1 stop5h 41m

Chicago Midway

Wed 7/9

9:24 am-3:30 pm

1 stop6h 06m

$199

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 6/27

4:14 pm-9:37 pm

1 stop5h 23m

Chicago O'Hare Intl

Wed 7/9

11:05 am-3:30 pm

1 stop4h 25m

$204

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 6/27

2:43 pm-4:03 pm

Nonstop1h 20m

Chicago O'Hare Intl

Tue 7/1

8:20 pm-9:35 pm

Nonstop1h 15m

$225

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 7/11

9:02 am-9:30 pm

1 stop12h 28m

Chicago O'Hare Intl

Fri 7/18

3:18 pm-10:19 pm

1 stop31h 01m

$230

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Mon 6/23

9:05 am-3:33 pm

1 stop6h 28m

$131

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Mon 9/1

6:35 pm-7:50 pm

Nonstop1h 15m

$192

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Fri 8/29

12:11 pm-5:37 pm

1 stop5h 26m

$214

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Thu 7/10

7:00 am-10:16 am

1 stop3h 16m

$214

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sat 6/21

12:55 pm-2:16 pm

Nonstop1h 21m

$280

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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 June 12, 2025.

The most flights from OS9 to CHI are scheduled on a Wednesday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
To help decide which airline to fly from Oshkosh to Chicago, see what other customers have to say about Delta, United Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,950 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Oshkosh to Chicago one-way?

    The cheapest airlines for a one-way flight from Oshkosh to Chicago are American Airlines ($192), Delta ($214), and United Airlines ($219).

  • 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: Envoy Air (100%), Avianca (85%), Copa Airlines (85%).

  • What are the cheapest flights from Oshkosh to Chicago?

    While on average a flight from Oshkosh to Chicago is generally $3,505, our data shows the cheapest flight currently is $102. 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 Oshkosh?

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

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$304FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$295FlexibilityNo cancel feeOn-time71%

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