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$125+ 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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — CHI
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Oshkosh to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Oshkosh (OS9) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$268
(Delta)

One-way from

$125
(American Airlines)

Popular in

October

Cheapest in

May

Average price

$299
From Oshkosh to Chicago (CHI)
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One-way flight from Oshkosh to Chicago (CHI)
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High demand for flights, 15% potential price rise
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Best time to find cheap flights, 6% potential price drop
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Average for round-trip flights in December 2024
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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 December 22, 2024.

This American Airlines deal was found by Cheapflights users on 12/21. 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 12/285:13 amATW - ORD
Nonstop1h 23mAmerican Airlines
Sat 1/43:20 pmORD - ATW
Nonstop1h 01mAmerican Airlines
Deal found 12/21$459
This Delta deal was found by Cheapflights users on 12/22. 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 12/271:05 pmATW - MDW
1 stop4h 39mDelta
Sun 12/295:04 pmMDW - ATW
1 stop5h 28mDelta
Deal found 12/22$523
This Delta deal was found by Cheapflights users on 12/21. 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 12/285:14 pmATW - ORD
1 stop4h 03mDelta
Sat 1/45:30 pmORD - ATW
1 stop3h 57mDelta
Deal found 12/21$548
This United Airlines deal was found by Cheapflights users on 12/21. 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 12/283:45 pmATW - ORD
Nonstop1h 23mUnited Airlines
Sat 1/410:50 amORD - ATW
1 stop9h 59mUnited Airlines
Deal found 12/21$602
This Mytrip deal was found by Cheapflights users on 12/22. 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.
Mon 12/236:00 amATW - ORD
1 stop14h 49mMultiple Airlines
Sat 12/289:35 pmORD - ATW
2 stops26h 03mMultiple Airlines
Deal found 12/22$749

Find flights from Oshkosh to Chicago within your budget

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Tue 1/28

11:30 am-4:13 pm

1 stop4h 43m

Chicago O'Hare Intl

Wed 2/5

10:30 am-4:35 pm

1 stop6h 05m

$268

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Thu 6/5

4:38 pm-5:50 pm

Nonstop1h 12m

Chicago O'Hare Intl

Sun 6/8

2:40 pm-3:40 pm

Nonstop1h 00m

$269

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Fri 1/17

5:34 pm-6:54 pm

Nonstop1h 20m

Chicago O'Hare Intl

Sun 1/19

7:40 pm-8:54 pm

Nonstop1h 14m

$309

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Thu 6/5

12:00 pm-5:03 pm

1 stop5h 03m

Chicago Midway

Sun 6/8

9:20 am-3:30 pm

1 stop6h 10m

$318

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sun 1/5

6:00 am-12:33 am

2 stops18h 33m

Chicago O'Hare Intl

Thu 1/9

6:55 am-3:01 pm

1 stop8h 06m

$460

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Wed 1/22

5:38 am-7:01 am

Nonstop1h 23m

$125

AppletonChicago

ATW - MDW

ATWMDW

Appleton Intl

Tue 2/4

12:20 pm-5:43 pm

1 stop5h 23m

$134

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sun 1/19

6:55 am-12:55 pm

1 stop6h 00m

$134

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Sun 1/19

5:34 pm-6:55 pm

Nonstop1h 21m

$155

AppletonChicago

ATW - ORD

ATWORD

Appleton Intl

Thu 4/24

7:30 am-7:22 pm

2 stops11h 52m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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.

Travel insights for flights from Oshkosh to Chicago

Get recent, data-driven insights about flights from Oshkosh to Chicago including ideal travel times, pricing trends, and more.

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 $317). 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 December 22, 2024.

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.

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 December 22, 2024.

The most flights from OS9 to CHI are scheduled on a Friday (43 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (19 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 December 22, 2024.
To help decide which airline to fly from Oshkosh to Chicago, see what other customers have to say about Delta, American Airlines and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,594 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,594 reviews
Delta
8.0
Very good
8,594 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
9,028 reviews
Delta
8.0
Very good
8,594 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,594 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

7.9

Food

7.3

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 ($125), Delta ($134), and United Airlines ($155).

  • 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: Avianca (94%), Qatar Airways (92%), Japan Airlines (91%).

  • What are the cheapest flights from Oshkosh to Chicago?

    While on average a flight from Oshkosh to Chicago is generally $1,236, our data shows the cheapest flight currently is $146. When looking at the most popular route, (Appleton Intl - Chicago O'Hare Intl), you can expect to pay $249 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 $317). 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.

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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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$176Average$309FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$178Average$282FlexibilityNo cancel feeOn-time69%
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