Flying to Chicago for the Holidays? Here’s When Midway Beats O’Hare, and When It Doesn’t

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The Midway vs O’Hare question comes up every time a Chicago holiday trip gets booked, and the honest answer depends on who you’re flying, where you’re going in the city, and what time you land. Both airports connect directly to downtown by CTA train, which makes Chicago the only US city with rapid transit to two major airports.

Here’s the short version. Midway beats O’Hare if you’re flying Southwest, heading downtown or to the South or Southwest Side, and want a smaller airport that’s quicker to get through. O’Hare beats Midway if you’re flying United or American, traveling internationally, need lots of nonstop options or backup flights, are staying on the North Side, or landing late at night.

Midway sits about 10 miles southwest of the Loop. O’Hare is roughly 17 to 18 miles northwest. That distance difference shows up in train time, rideshare costs, and how long the trip into the city feels after a long travel day.

When Midway Beats O’Hare, and When It Doesn’t

Here’s how the two airports compare on the factors that matter most for a holiday trip.

Midway wins if you fly Southwest

Midway is Southwest Airlines’ largest base, and Southwest carries the overwhelming majority of the airport’s passengers. If you’re flying Southwest into Chicago, you’ll almost certainly land at Midway, with nonstop service to dozens of US cities. Southwest does operate some flights at O’Hare, but Midway is where its Chicago schedule lives. Delta, Frontier, Porter, Allegiant, and a few others also serve Midway.

Midway wins on getting downtown

According to the Chicago Transit Authority, the Orange Line from Midway reaches downtown in about 20 to 25 minutes, and the fare is $2.50 or less. The station connects to the terminal by an enclosed walkway. The Blue Line from O’Hare takes about 40 to 45 minutes to downtown and costs up to $5 when you board at the airport.

Rideshare follows the same pattern. The CTA estimates rideshare from Midway to downtown at around $25 to $40 and from O’Hare at around $35 to $50, with surge pricing pushing both much higher at peak times. Holiday weekends and bad weather are prime surge times.

Midway wins on size

Midway has one terminal with three concourses, so walks from the curb to the gate are short. O’Hare has multiple terminals, long concourses, and a train system to connect them, and getting from security to a distant gate can take a while. On a busy holiday day, a smaller airport means less walking and less confusion, which matters if you’re traveling with kids, older relatives, or lots of bags.

O’Hare wins if you fly United or American

O’Hare is a major hub for both United and American. If you’re on either airline, or you care about elite status and upgrades, O’Hare is where you’ll find their full schedules. It also has many more flights overall, roughly five times as many as Midway by some estimates.

O’Hare wins for international trips

O’Hare handles nearly all of Chicago’s long-haul international service, with flights to Europe, Asia, the Middle East, and Latin America, and Terminal 5 serves most international carriers. Midway has only limited near-international service. If your holiday trip includes an international leg, O’Hare is almost always the choice.

O’Hare wins when things go wrong

This is the factor holiday travelers underrate. When a storm cancels flights, your rebooking options depend on how many other flights your airline has to the same place. At O’Hare, United and American may have many daily flights on popular routes, plus partner airlines. At Midway, Southwest has a strong schedule, but on a sold-out holiday weekend, fewer total flights can mean fewer open seats to move into.

O’Hare wins for late-night arrivals

The Blue Line runs 24 hours a day, seven days a week, with trains from O’Hare going through downtown. The Orange Line from Midway doesn’t run overnight. The CTA’s schedule has the last train leaving Midway around 12:50 a.m. most nights and earlier on Sunday nights. If your flight lands after that, you’ll need a bus, taxi, or rideshare from Midway.

It depends on where you’re staying

Midway is closer to the South Side, Southwest Side, and southwest suburbs. O’Hare is closer to the North Side and northwest suburbs, and the Blue Line runs through neighborhoods like Logan Square and Wicker Park. If your family lives in the northwest suburbs, O’Hare can be the shorter trip. If they’re in the south suburbs or near Midway, the smaller airport is a clear win.

Winter Weather at Both Airports

Both airports deal with lake-effect snow, ice, and wind, and both de-ice planes in storms. O’Hare has more runways after a long modernization program, which helps it keep traffic moving, though its flight volume also means delays can ripple across the national system. Midway’s runways are shorter and its airfield tighter, since it’s boxed in by city neighborhoods.

In practice, weather delays hit both airports. The bigger difference during a storm is the rebooking math: how many alternative flights your airline has from that airport.

A Note on Alternative Airports

If neither Chicago airport fits, some travelers look farther afield. Chicago Rockford International Airport, about 90 miles northwest of the Loop, has limited leisure service on carriers like Allegiant. Milwaukee Mitchell International Airport is about 90 minutes north and connects by Amtrak’s Hiawatha service to downtown Chicago. Both can make sense for specific routes or fares, but they add travel time.

Traveling Between the Two Airports

Some itineraries land at one airport and leave from the other, especially when you’re mixing airlines. Don’t plan a tight connection between them. The airports are about 30 miles apart by road.

By CTA, you can take the Orange Line from Midway downtown, transfer free to the Blue Line at Clark/Lake, and ride out to O’Hare. Chicago’s airport authority advises allowing up to two hours for that trip. A taxi or rideshare is faster outside rush hour but can be expensive, and traffic on the Kennedy and Stevenson expressways can be heavy.

Midway vs O’Hare: A Quick Decision Guide

Choose Midway if:

• You’re flying Southwest.
• You’re staying downtown, on the South or Southwest Side, or in the southwest suburbs.
• You want the smallest, simplest airport experience.
• You land before the Orange Line stops running.

Choose O’Hare if:

• You’re flying United or American, or any international flight.
• You want the most nonstop routes and backup options.
• You’re staying on the North Side or in the northwest suburbs.
• You might land late at night and want the 24-hour Blue Line.

Security and Holiday Crowds

On peak days like the Wednesday before Thanksgiving or the Sunday after, both airports get crowded. O’Hare’s scale means it has more checkpoints, but it also has far more passengers. Midway’s single terminal means one main set of checkpoints, which can back up when several Southwest flights depart at once.

A few things help at either one:

• Check your airline app or the airport’s website for estimated security wait times on the morning of your flight.
• Use TSA PreCheck if you have it. Both airports have PreCheck lanes.
• Arrive at least two hours before a domestic flight on peak days.
• At O’Hare, make sure you go to the right terminal. United and American mostly use Terminals 1 and 3, while Terminal 5 handles most international departures and some domestic carriers.

Parking and Pickups

If someone is driving you, both airports have cell phone waiting lots where drivers can wait free until you’re at the curb. Holiday arrivals are a crush, and circling the terminal roads adds to traffic.

Parking costs vary by lot. Both airports offer economy lots with shuttles and garage parking closer to the terminals, and daily rates in the garages are higher. For a multi-day holiday trip, economy lots or the train usually make more sense. Check current rates on the Chicago Department of Aviation’s FlyChicago website before you go.

Holiday Tips for Either Airport

Whichever you pick, a few habits make a Chicago holiday trip smoother:

• Check your departure terminal at O’Hare before you leave. Airlines operate from different terminals, and moving between them takes time.
• Take the train when you can. Expressway traffic around the holidays, especially the day before Thanksgiving, is notoriously slow.
• Download your airline’s app and turn on notifications for gate and delay changes.
• Arrive at least two hours early on peak travel days.
• If you’re picking someone up, use the airport’s cell phone waiting lot instead of circling arrivals.

The Bottom Line

One more factor: price. Fares vary by route and date, and on some routes Southwest at Midway is cheaper, while on others United or American at O’Hare comes in lower. Always compare both airports when you search, and factor in the cost of getting to and from each one. A cheaper fare into O’Hare can disappear if it means a $60 surge-priced ride to the South Side.

Midway is the easier airport, and for Southwest travelers headed downtown or to the South Side, it usually wins. O’Hare is the bigger, more connected airport, and for United and American flyers, international travelers, North Side visitors, and anyone who wants backup flights during a storm, it usually wins. Match the airport to your airline and your final destination, and the holiday trip gets a lot simpler.