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Oshkosh

Cheap flights from Chicago (CHI) to Oshkosh, WI

CHI — MKE
Nov 14 — Nov 211
Sat 11/14
Sat 11/21
1 adult, Economy
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FlightHub
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FlightHub
3 stars
Provider with most accurate pricing for Chicago (CHI)-Appleton Intl flight deals.
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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?

It’s optimal to fly from Chicago to Oshkosh in the evening. By choosing this option you can save up to 24% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Chicago to Oshkosh?

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 at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Oshkosh

Get a feel of what it's like to fly with United Airlines from Chicago to Oshkosh by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,362 reviews

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible
United Airlines
7.4
Good
10,362 reviews
United Airlines
7.4
Good
10,362 reviews

Entertainment

7.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.7

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Dawn,Aug 2026

ORD - DEN

I missed my connecting flight because our plane took off ten minutes late and then when we got to the airport another plane was in our shoot waiting to get fueled up and that took 30 minutes so I missed my connecting flight. I asked if I could get off and they assured me the plane would most likely wait for me since they know what time the planes get in because of an app. I was not happy. I had to wait till 7:25 to board the next flight and then that was delayed. Gates changed till 9:20. Terrible

Related info for your journey

  • 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: Republic Airways (100%), Avianca (74%), Aer Lingus( 72%).

  • What are the cheapest flights from Chicago to Oshkosh?

    Looking at all options, your cheapest flight can be booked for $234. While the most popular route (Chicago O'Hare Intl - Appleton Intl) can be booked for $309 on average, our data indicates $289 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

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Top 2 airlines flying from Chicago to Oshkosh

AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$179Average$348FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$179Average$420FlexibilityNo cancel feeOn-time69%

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