Highlighted price = Cheapest round-trip flights
Prices are round trip per person (conditions apply)
Save more with Chicago Flight + Hotel packages
Best Western Grant Park
Winnipeg ChicagoLeave Thu, Jul 23 - Return Mon, Jul 27Chicago+$792.005 days, 4 nights per person
Wyndham Grand Chicago Riverfront
Winnipeg ChicagoLeave Mon, Sep 7 - Return Sat, Sep 12ChicagoSummer Sale - Save 25% on your stay+$878.006 days, 5 nights per person
MileNorth, A Chicago Hotel
Winnipeg ChicagoLeave Thu, Jul 23 - Return Mon, Jul 27Chicago+$936.005 days, 4 nights per person
Winnipeg ChicagoLeave Mon, Sep 7 - Return Sat, Sep 12ChicagoBook early and save 10% on your stay+$930.006 days, 5 nights per person
Winnipeg ChicagoLeave Mon, Sep 7 - Return Sat, Sep 12ChicagoSave 15% on your stay+$807.006 days, 5 nights per person
The Godfrey Hotel Chicago
Winnipeg ChicagoLeave Mon, Sep 7 - Return Sat, Sep 12Chicago+$881.006 days, 5 nights per person
The Talbott Hotel
Winnipeg ChicagoLeave Mon, Sep 7 - Return Sat, Sep 12ChicagoLast Minute Deal!+$862.006 days, 5 nights per person
Congress Plaza Hotel at Grant Park
Winnipeg ChicagoLeave Thu, Jul 23 - Return Mon, Jul 27ChicagoSave 10% on your stay+$743.005 days, 4 nights per person
Chicago's Essex Inn
Winnipeg ChicagoLeave Mon, Sep 7 - Return Sat, Sep 12ChicagoSave 15% on your stay+$719.006 days, 5 nights per person
Inn of Chicago, an Ascend Collection hotel
Winnipeg ChicagoLeave Mon, Sep 7 - Return Sat, Sep 12Chicago+$802.006 days, 5 nights per person
Warwick Allerton Hotel Chicago
Winnipeg ChicagoLeave Mon, Sep 7 - Return Sat, Sep 12Chicago+$732.006 days, 5 nights per person
Millennium Knickerbocker Hotel Chicago
Winnipeg ChicagoLeave Mon, Sep 7 - Return Sat, Sep 12ChicagoSave 15% on your stay+$798.006 days, 5 nights per person
Winnipeg and Chicago airports and terminals
Airports in Winnipeg MB, CA
Winnipeg Airport (YWG)
Distance from City Center: 3.8 miles
Carriers for flights from YWG to CHI
CarriersAir Canada, United Airlines
Airports in Chicago IL, US
Midway Airport (MDW)
Distance from City Center: 9.5 miles
O'Hare International Airport (ORD)
Distance from City Center: 15.1 miles
Terminals and carriers for flights from YWG to ORD
Terminal Carriers Terminal 1 Air Canada, United Airlines Terminal 2 Air Canada, United Airlines
Featured Chicago Airport Hotels
O'Hare International Airport Map
Rate Includes Breakfast
...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More
6500 South Cicero Avenue Map
Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More
6530 S. Cicero Avenue Map
Complimentary wired and Wi-Fi Internet Access
...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More
6540 S. Cicero Ave. Map
Free On The HouseT hot breakfast, Wi-Fi
...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More
Flights to Chicago
James Armstrong Richardson International Airport in Winnipeg, MN
Twenty airlines provide international and domestic flights from the James Armstrong Richardson International Airport, which is the main airport that serves Winnipeg, Manitoba, Canada. Cheap flights from Winnipeg that are available through Orbitz.com usually depart from this major airport.
Parking at James Armstrong Richardson Airport
There are two parking facilities at James Armstrong Richardson Airport. One is a large economy lot with lower prices for long-term parking, and the other is smaller and known as the Parkade. You can treat yourself to valet parking for an extra 25 Canadian dollars at the Parkade, where the fees are 20 Canadian dollars per day and 90 dollars per week. Weekly fees are 75 Canadian dollars and daily fees are 15 dollars at the economy lot, and the short-term parking fee at either lot is two Canadian dollars per half-hour.
Transportation to James Armstrong Richardson Airport
Winnipeg Transit operates city buses from various points in Winnipeg to the airport. Bus tickets are available from authorized vendors for 2.15 Canadian dollars, or you can pay 2.45 dollars cash on the bus itself. A private shuttle is also available from the town of Brandon for 48 Canadian dollars. Unicity is the official airport taxi service, and its rates range from 9.25 to 32 Canadian dollars depending on the distance traveled. Limousines and private shuttles are also available. Whether you choose the bargain bus or a luxury limousine, you can relax on your way to the airport knowing everything is ready for you when you book your tickets and other travel needs through Orbitz.com.
Restaurants at James Armstrong Richardson Airport
There are nine dining options at this airport, including Starbucks Coffee, T.G.I. Friday's, Tim Hortons, a local pizzeria, a bar and an Oriental fast-food restaurant. This gives you a wide choice of food and drink to enjoy before you board the flight that you selected from the cheap flights from Winnipeg that are featured on Orbitz.com.
Airports in Chicago
Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.
Transportation from the Airport
Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.
Weather in Chicago
Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.
Highlights and Attractions
Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.
Interesting facts about flights from Winnipeg to Chicago
- 6 direct flights are operating from Winnipeg to Chicago today.
- Today's average time for a direct flight is 2h 8m.
- Air Canada flight 4117 (7:27 AM GMT, Canadair Regional Jet) is today's earliest available flight from Winnipeg to Chicago.
- Air Canada flight 4499 (5:36 PM GMT, Canadair Regional Jet) is today's latest available flight from Winnipeg to Chicago.
- Today's shortest direct flight from Winnipeg to Chicago (Air Canada flight 4117, Canadair Regional Jet) takes 2h 7m.
- Today's longest direct flight from Winnipeg to Chicago (Air Canada flight 4423, Canadair Regional Jet) takes 2h 11m.
- Flights from Winnipeg Airport (YWG) to Midway Airport (MDW), O'Hare International Airport (ORD) are available for this route.
Promo Code Terms and Conditions
Book a qualifying 4-night flight + hotel vacation package between June 1, 2015 12:00AM CST and September 30, 2015 11:59PM CST, for $1000 or more for travel between June 1, 2015 and December 31, 2015 via Orbitz and instantly receive $125 off the hotel portion of your booking through the use of the promotion code. Limit one discount per hotel room and one promotion code per booking. Discounts are not redeemable for cash for any reason. Promotion codes cannot be resold. Any attempt at fraud will be prosecuted to the fullest extent of the law. Void where prohibited, taxed or restricted. Orbitz reserves the right to change or limit the promotion in its sole discretion. Promo code not valid for Las Vegas, NV bookings.
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. 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.