
$117 Cheap flight deals from Chicago (CHI) to Windsor (OAK)
Earn rewards on top of your airline miles with Orbitz Rewards
Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
This Weekend's Flight Deals from Chicago to Windsor
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $117 One Way, $260 Round Trip from Chicago to Windsor
Prices starting at $260 for return flights and $117 for one-way flights to Windsor were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Windsor economy flight packages

Claremont Resort & Club
Dec 19 - Dec 21
Chicago (ORD) to Oakland (OAK)
Oakland (OAK) to Chicago (ORD)
Reviewed on May 25, 2024

Fairmont Sonoma Mission Inn & Spa
Dec 20 - Dec 23
Chicago (ORD) to Oakland (OAK)
Reviewed on May 31, 2023

Stanly Ranch, Auberge Collection
Dec 1 - Dec 5
Chicago (CHI) to Oakland (OAK)
Oakland (OAK) to Chicago (CHI)
Reviewed on Jul 18, 2025
More About Flying To Windsor from Chicago
Route Information for Flights from Chicago to Windsor
| Origin Airport IATA Code | CHI | 
|---|---|
| Destination Airport IATA Code | OAK | 
| Distance | |
| Direct Flight Airlines | |
| Earliest Flight Arrival | |
| Latest Flight Arrival | 
Chicago to Windsor
Those who want guaranteed low prices for Chicago to Windsor flights only need to visit Orbitz. We take advantage of the latest mobile technologies to make sure you get the best bargain on your trip and that everything goes smoothly and according to your plans.
Take Advantage of Orbitz’s Amazing Customer Service on Chicago to Windsor Flights
We will help you from booking to boarding on flights from Chicago to Windsor. Whether you have questions about baggage limits, seat assignments or anything else, we will be there to answer them for you.
Get Great Recommendations For Travel Ideas On Orbitz.com
We do not only get the best bargains on flights from Chicago to Windsor, but we can tell you what to do once you get there. Whether it is a music festival, hotel recommendation or list of local attractions, Orbitz can help make your travel plan more exciting.
Combine Car Rental With Your Discount Flight For Even More Savings
Not only can we get bargain deals on flights from Chicago to Windsor but we can book your transport as well. By combining car rental with Chicago to Windsor flights, you can be sure to save money and start moving as soon as you hit the ground.
Use Orbitz On The Go To Stay Informed Using Your Smartphone
This convenient app works with most smartphones and allows you to see the status of flights from Chicago to Windsor. You don’t have to worry, if something goes wrong, we’ll let you know.
Flights from Chicago
- Chicago to Orlando
- Chicago to Houston
- Chicago to New York
- Chicago to Phoenix
- Chicago to Dallas
- Chicago to Los Angeles
- Chicago to London
- Chicago to New Orleans
- Chicago to Washington
- Chicago to Rome
- Chicago to Paris
- Chicago to Toronto
- Chicago to San Francisco
- Chicago to Cleveland
- Chicago to Detroit
- Chicago to Montreal
- Chicago to Sacramento
- Chicago to Kansas City
- Chicago to Hartford
- Chicago to Atlantic City
Windsor Airports
More Destinations
- Flights from Nantucket (ACK) to Santa Rosa (STS)
- Flights from Albany (ALB) to Santa Rosa (STS)
- Flights from Anchorage (ANC) to Santa Rosa (STS)
- Flights from Atlanta (ATL) to Santa Rosa (STS)
- Flights from Austin (AUS) to Santa Rosa (STS)
- Flights from St. George's (BDA) to Santa Rosa (STS)
- Flights from Bishop (BIH) to Santa Rosa (STS)
- Flights from Broomfield (BJC) to Santa Rosa (STS)
- Flights from Bemidji (BJI) to Santa Rosa (STS)
- Flights from Beaumont (BMT) to Santa Rosa (STS)
- Flights from Nashville (BNA) to Santa Rosa (STS)
- Flights from Boston (BOS) to Santa Rosa (STS)
- Flights from Burlington (BTV) to Santa Rosa (STS)
- Flights from Burbank (BUR) to Santa Rosa (STS)
- Flights from Charleston (CHS) to Santa Rosa (STS)
- Flights from Charleston (CRW) to Santa Rosa (STS)
- Flights from Sapporo (CTS) to Santa Rosa (STS)
- Flights from Dayton (DAY) to Santa Rosa (STS)
- Flights from Dubuque (DBQ) to Santa Rosa (STS)
- Flights from Denver (DEN) to Santa Rosa (STS)
- Flights from Dallas (DFW) to Santa Rosa (STS)
- Flights from Durango (DGO) to Santa Rosa (STS)
- Flights from Des Moines (DSM) to Santa Rosa (STS)
- Flights from Phoenix (DVT) to Santa Rosa (STS)
- Flights from Kalispell (FCA) to Santa Rosa (STS)
- Flights from Fort Lauderdale (FLL) to Santa Rosa (STS)
- Flights from Sioux Falls (FSD) to Santa Rosa (STS)
- Flights from Guadalajara (GDL) to Santa Rosa (STS)
- Flights from Hartford (HFD) to Santa Rosa (STS)
- Flights from Lake Havasu City (HII) to Santa Rosa (STS)
- Flights from Hong Kong (HKG) to Santa Rosa (STS)
- Flights from Honolulu (HNL) to Santa Rosa (STS)
- Flights from Hays (HYS) to Santa Rosa (STS)
- Flights from Houston (IAH) to Santa Rosa (STS)
- Flights from Islip (ISP) to Santa Rosa (STS)
- Flights from New York (JFK) to Santa Rosa (STS)
- Flights from Jiansanjiang (JSJ) to Santa Rosa (STS)
- Flights from Kigali (KGL) to Santa Rosa (STS)
- Flights from Las Vegas (LAS) to Santa Rosa (STS)
- Flights from Los Angeles (LAX) to Santa Rosa (STS)
- Flights from Labasa (LBS) to Santa Rosa (STS)
- Flights from New York (LGA) to Santa Rosa (STS)
- Flights from London (LGW) to Santa Rosa (STS)
- Flights from Madrid (MAD) to Santa Rosa (STS)
- Flights from Midland (MAF) to Santa Rosa (STS)
- Flights from Kansas City (MCI) to Santa Rosa (STS)
- Flights from Orlando (MCO) to Santa Rosa (STS)
- Flights from Meridian (MEI) to Santa Rosa (STS)
- Flights from Monroe (MLU) to Santa Rosa (STS)
- Flights from Modesto (MOD) to Santa Rosa (STS)
- Flights from Minot (MOT) to Santa Rosa (STS)
- Flights from Minneapolis (MSP) to Santa Rosa (STS)
- Flights from New Orleans (MSY) to Santa Rosa (STS)
- Flights from Myrtle Beach (MYR) to Santa Rosa (STS)
- Flights from Oakland (OAK) to Santa Rosa (STS)
- Flights from Olympia (OLM) to Santa Rosa (STS)
- Flights from Omaha (OMA) to Santa Rosa (STS)
- Flights from Ontario (ONT) to Santa Rosa (STS)
- Flights from Chicago (ORD) to Santa Rosa (STS)
- Flights from Seattle Paine Field Intl. Airport (PAE) to Santa Rosa (STS)
- Flights from West Palm Beach (PBI) to Santa Rosa (STS)
- Flights from Paraburdoo (PBO) to Santa Rosa (STS)
- Flights from Portland (PDX) to Santa Rosa (STS)
- Flights from Philadelphia (PHL) to Santa Rosa (STS)
- Flights from Phoenix (PHX) to Santa Rosa (STS)
- Flights from Pasco (PSC) to Santa Rosa (STS)
- Flights from Palm Springs (PSP) to Santa Rosa (STS)
- Flights from Pueblo (PUB) to Santa Rosa (STS)
- Flights from Provo (PVU) to Santa Rosa (STS)
- Flights from Richmond (RIC) to Santa Rosa (STS)
- Flights from Rochester (ROC) to Santa Rosa (STS)
- Flights from Fort Myers (RSW) to Santa Rosa (STS)
- Flights from Santa Fe (SAF) to Santa Rosa (STS)
- Flights from San Diego (SAN) to Santa Rosa (STS)
- Flights from San Antonio (SAT) to Santa Rosa (STS)
- Flights from San Luis Obispo (SBP) to Santa Rosa (STS)
- Flights from Scottsdale (SCF) to Santa Rosa (STS)
- Flights from Louisville (SDF) to Santa Rosa (STS)
- Flights from Santo Domingo (SDQ) to Santa Rosa (STS)
- Flights from Seattle (SEA) to Santa Rosa (STS)
- Flights from Orlando (SFB) to Santa Rosa (STS)
- Flights from San Jose (SJC) to Santa Rosa (STS)
- Flights from Salt Lake City (SLC) to Santa Rosa (STS)
- Flights from Sacramento (SMF) to Santa Rosa (STS)
- Flights from Orange County (SNA) to Santa Rosa (STS)
- Flights from St. Louis (STL) to Santa Rosa (STS)
- Flights from Silver City (SVC) to Santa Rosa (STS)
- Flights from Syracuse (SYR) to Santa Rosa (STS)
- Flights from Truckee (TKF) to Santa Rosa (STS)
- Flights from Tallahassee (TLH) to Santa Rosa (STS)
- Flights from Tri-Cities (TRI) to Santa Rosa (STS)
- Flights from Trenton (TTN) to Santa Rosa (STS)
- Flights from Concord (USA) to Santa Rosa (STS)
- Flights from Van Nuys (VNY) to Santa Rosa (STS)
- Flights from Selawik (WLK) to Santa Rosa (STS)
- Flights from Watsonville (WVI) to Santa Rosa (STS)
- Flights from Fayetteville (XNA) to Santa Rosa (STS)
- Flights from Campbell River (YBL) to Santa Rosa (STS)
- Flights from Vancouver (YVR) to Santa Rosa (STS)
- Flights from St. John's (YYT) to Santa Rosa (STS)
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

