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$105+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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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 November 26, 2025.

This American Airlines deal was found by Cheapflights users on 11/24. 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 12/169:39 amATW - ORD
Nonstop1h 25mAmerican Airlines
Sat 12/208:05 amORD - ATW
Nonstop1h 16mAmerican Airlines
Deal found 11/24$179
This American Airlines deal was found by Cheapflights users on 11/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:58 pmATW - ORD
Nonstop1h 28mAmerican Airlines
Sun 12/218:05 amORD - ATW
Nonstop1h 16mAmerican Airlines
Deal found 11/25$194
This American Airlines deal was found by Cheapflights users on 11/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:10 amATW - ORD
Nonstop1h 24mAmerican Airlines
Sun 12/148:05 amORD - ATW
Nonstop1h 03mAmerican Airlines
Deal found 11/25$209
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2411:00 amATW - ORD
1 stop6h 22mDelta
Wed 12/316:35 amORD - ATW
1 stop4h 57mDelta
Deal found 11/25$214
This Delta deal was found by Cheapflights users on 11/24. 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.
Sat 12/134:18 pmATW - ORD
1 stop5h 22mDelta
Sun 12/146:45 amORD - ATW
1 stop3h 48mDelta
Deal found 11/24$229
This American Airlines deal was found by Cheapflights users on 11/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:08 pmATW - ORD
Nonstop1h 26mAmerican Airlines
Sun 12/710:24 pmORD - ATW
Nonstop1h 10mAmerican Airlines
Deal found 11/25$239
This American Airlines deal was found by Cheapflights users on 11/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:51 amATW - ORD
Nonstop1h 24mAmerican Airlines
Sun 12/2810:30 pmORD - ATW
Nonstop1h 06mAmerican Airlines
Deal found 11/25$241
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:13 amATW - ORD
1 stop5h 09mDelta
Sun 12/76:45 amORD - ATW
1 stop3h 48mDelta
Deal found 11/25$259
This American Airlines deal was found by Cheapflights users on 11/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/275:20 amATW - ORD
Nonstop1h 19mAmerican Airlines
Sat 11/298:10 amORD - ATW
Nonstop1h 06mAmerican Airlines
Deal found 11/25$262
This Delta deal was found by Cheapflights users on 11/26. 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 12/1012:20 pmATW - MDW
1 stop5h 58mDelta
Sat 12/131:14 pmMDW - ATW
1 stop4h 15mDelta
Deal found 11/26$264
This Delta deal was found by Cheapflights users on 11/23. 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 12/1011:13 amATW - ORD
1 stop5h 46mDelta
Sun 12/146:00 amORD - ATW
1 stop5h 40mDelta
Deal found 11/23$264
This United Airlines deal was found by Cheapflights users on 11/24. 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 12/103:42 pmATW - ORD
Nonstop1h 28mUnited Airlines
Sun 12/1412:45 pmORD - ATW
Nonstop1h 12mUnited Airlines
Deal found 11/24$269

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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$179
(American Airlines)

One-way from

$105
(Kiwi.com)

Popular in

January

Cheapest in

July

Average price

$344
Provider with most accurate pricing for Appleton Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Appleton Intl-Chicago (CHI) flights.
Search Deals
From Oshkosh to Chicago (CHI)
Search Deals
One-way flight from Oshkosh to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 November 26, 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

Wed 12/24

7:25 am-8:55 am

Nonstop1h 30m

Chicago O'Hare Intl

Wed 12/31

8:05 am-9:21 am

Nonstop1h 16m

$179

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 1/9

12:35 pm-2:07 pm

Nonstop1h 32m

Chicago O'Hare Intl

Sat 1/24

6:01 pm-7:15 pm

Nonstop1h 14m

$179

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 1/9

6:32 pm-8:11 pm

Nonstop1h 39m

Chicago O'Hare Intl

Tue 1/20

4:53 pm-6:01 pm

Nonstop1h 08m

$179

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sat 2/7

5:04 pm-6:39 pm

Nonstop1h 35m

Chicago O'Hare Intl

Sat 2/14

9:05 am-10:13 am

Nonstop1h 08m

$179

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Tue 12/16

9:39 am-11:04 am

Nonstop1h 25m

Chicago O'Hare Intl

Sat 12/20

8:05 am-9:21 am

Nonstop1h 16m

$179

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Wed 2/18

3:45 pm-5:10 pm

Nonstop1h 25m

Chicago O'Hare Intl

Sun 2/22

3:35 pm-4:44 pm

Nonstop1h 09m

$194

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 2/20

6:31 pm-7:59 pm

Nonstop1h 28m

Chicago O'Hare Intl

Mon 3/9

10:20 pm-11:25 pm

Nonstop1h 05m

$194

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Fri 1/9

6:45 am-12:48 pm

1 stop6h 03m

Chicago Midway

Sat 1/24

11:45 am-3:40 pm

1 stop3h 55m

$199

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 1/9

12:03 pm-9:05 pm

2 stops9h 02m

Chicago O'Hare Intl

Tue 1/20

1:58 pm-8:49 pm

1 stop6h 51m

$204

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Wed 12/10

5:10 am-6:34 am

Nonstop1h 24m

Chicago O'Hare Intl

Sun 12/14

8:05 am-9:08 am

Nonstop1h 03m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 35 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, February is the cheapest month in which you can book a flight from Oshkosh to Chicago (average of $179). Flying from Oshkosh to Chicago in March is currently the most expensive (average of $215). 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 November 26, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 34% on flights from Oshkosh to Chicago by exploring options for tickets in the morning.

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 Thursday mornings 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 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 November 26, 2025.

The most flights from OS9 to CHI are scheduled on a Monday (57 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (5 on average).

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 November 26, 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
9,050 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
9,050 reviews
United Airlines
7.4
Good
9,050 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,038 reviews
United Airlines
7.4
Good
9,050 reviews

Comfort

7.3

Crew

8.1

Overall

7.4

Entertainment

7.1

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 30m. 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: Iberia (86%), Copa Airlines (75%), Air New Zealand (74%).

  • What are the cheapest flights from Oshkosh to Chicago?

    While on average a flight from Oshkosh to Chicago is generally $1,053, our data shows the cheapest flight currently is $118. 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, February is the cheapest month in which you can book a flight from Oshkosh to Chicago (average of $179). Flying from Oshkosh to Chicago in March is currently the most expensive (average of $215). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$179Average$285FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$179Average$274FlexibilityNo cancel feeOn-time71%

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