Cheap flights from Oshkosh, WI to Chicago (CHI)
MKE — CHI
Nov 27 — Dec 41
Round-trip
1 adult, Economy
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Keep the following information in mind while searching for Oshkosh to Chicago flight deals. Data was last updated October 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Popular in | October |
Cheapest in | February |
Average price | $397 |
Cheapflights Insights
Everything you need to know about your flight from Oshkosh to Chicago
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 October 28, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 14% 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 October 24, 2026.
Travelers seeking maximum savings on their Oshkosh to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 October 28, 2026.
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.
Boarding
7.7
Crew
8.1
Food
6.7
Comfort
7.3
Overall
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Crew
8.1
Food
6.7
Comfort
7.3
Overall
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Crew
8.1
Food
6.7
Comfort
7.3
Overall
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Oshkosh and Chicago flights
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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 7,457,451 searches. Data last updated October 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$171 | Average$293 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$179 | Average$311 | FlexibilityNo cancel fee | On-time71% |