Flight Deals from Toronto Island Airport to Chicago Midway Airport from $149

A direct flight from Toronto (YTZ) to Chicago (MDW) typically takes about 1 hour 15 minutes. Flights with common layovers, such as in other U.S. cities, can take between 3 to 5 hours including layover time.

Yes. Non-stop flights from Toronto to Chicago operate daily, with a flight duration of approximately 1 hour 30 minutes. Air Canada and Southwest Airlines are the primary carriers offering these direct services. Non-stop fares tend to be slightly higher than one-stop options, which may add about 10-20% to the price.

Chicago Midway Airport provides several ground transportation options. The CTA Orange Line train connects the airport to downtown Chicago in approximately fifteen minutes and is the most used and economical choice. Taxis and ride-share services are readily available outside the terminals, offering door-to-door service in about twenty minutes, depending on traffic. Car rentals are also available at the airport for those needing flexibility beyond the city. Buses and shuttles are available but less direct. The most popular option among travelers is the CTA Orange Line train for its speed, cost-effectiveness, and convenience.

Fares are usually lowest from January to March and in late fall. Midweek afternoon flights tend to be less expensive; booking one to three months ahead maximizes savings.

Book three to six weeks in advance for regular travel and six to eight weeks during summer peak and holiday seasons.

Air Canada and Southwest Airlines offer nonstop flights; United and American provide one‑stop options via their hubs.

Common layovers are Minneapolis, Detroit, Dallas and Denver, offering broad connections and efficient transfers.

On‑time departures are usually reliable, but peak hours may cause delays. Booking early morning flights can improve on‑time chances, with Air Canada and Southwest often performing well.

May to June and September offer mild weather and fewer tourists.

Bring a valid passport or equivalent accepted ID, ensure it meets the travel validity requirements, carry payment method for baggage, and have proof of onward or return travel. No visa required for US and Canadian citizens for short visits.

Midway Airport is closer to downtown Chicago and popular attractions, mainly serving domestic and low-cost carriers. O'Hare is larger with extensive international and domestic flights, ideal for business travelers.

To get to Billy Bishop Toronto City Airport from downtown, walk or take a short ferry ride across the harbor. Taxis and ride‑shares are also options but less common. The ferry is quick and popular.

Midway Airport has no on-site hotels, capsules, or sleeping pods. Nearby hotels include the Hyatt Place Chicago Midway Airport and the Holiday Inn Express Chicago Midway, accessible via shuttle.

Midway Airport offers currency exchange services, a prayer room in the main terminal, and free Wi‑Fi throughout.

Toronto Billy Bishop Airport offers accessible services, including wheelchair assistance, which should be requested at least 48 hours in advance. Chicago Midway provides similar assistance, with requests made through your airline 48 hours prior; both airports feature children’s play areas and family services.

Common aircraft on Toronto to Chicago routes include Embraer E175 and Bombardier CRJ900. Airlines like Air Canada and Southwest offer Wi‑Fi.

Afternoon flights on weekdays are typically cheaper than morning or evening departures.

At Toronto Billy Bishop Airport, the available lounges include the Air Canada Maple Leaf Lounge for eligible Air Canada business‑class passengers, elite members, and Star Alliance Gold members. It offers comfortable seating, refreshments, and Wi-Fi. Some lounges may offer pay‑per‑visit access for non‑members. Toronto's smaller airport has limited lounge options compared to larger hubs.

Baggage allowances on Toronto–Chicago flights depend on the airline and fare class. Basic economy may not include checked baggage; standard economy usually includes one checked bag and a carry‑on. Higher fares offer more baggage options.

Flights from Toronto to Chicago generally include Economy and Business class, with Premium Economy available on select airlines.

Policies vary by airline and ticket class; flexible fares and premium cabins generally offer better options for same‑day changes or standby, while basic fares often do not.