O'Hare vs Midway from Milwaukee: which is the easier trip?

Both of Chicago's major airports are within reach of Milwaukee, but they are not equally easy to get to. If your flight gives you a choice between O'Hare and Midway, here is how the two stack up for a Wisconsin traveler.

The quick answer

For most Milwaukee travelers, O'Hare is the easier drive even though it is technically a similar distance, because Midway sits deeper inside Chicago and the final approach runs through heavier city traffic. But the right choice depends on your flight, your airline, and where in the metro you are starting from.

Distance and drive time

On paper the two airports are a similar distance from Milwaukee, but the drive times differ. O'Hare is roughly 80 miles and about 90 minutes. Midway is around 93 miles and closer to an hour and 50 minutes, because reaching it means pushing further south past O'Hare and into denser Chicago traffic. That extra distance and congestion is the main reason O'Hare feels easier from Wisconsin.

Traffic and the approach

This is where O'Hare wins for most trips. The drive down I-94 is similar for both until you get close to Chicago. O'Hare sits on the northwest side, so you reach it before the worst of the city traffic. Midway is on the southwest side, which means crossing through or around more of the metro to get there. Our Milwaukee to Midway page covers how we plan around that heavier approach.

Airlines and flights

Midway is Southwest Airlines' Chicago hub, so if you are flying Southwest, Midway is often your airport by default, and the smaller, single-terminal layout can actually be quicker to move through once you arrive. O'Hare serves nearly every other major airline, offers far more nonstop destinations, and handles international travel. Let your flight options drive the decision as much as the geography.

Which should you choose?

Choose O'Hare if:

• You want the most nonstop and international options
• You are flying an airline other than Southwest
• You want the shorter, more predictable drive from Milwaukee

Choose Midway if:

• You are flying Southwest
• The fare or schedule is meaningfully better
• You prefer a smaller, simpler airport to navigate

Cost from Milwaukee

Because Midway is the longer drive, car service rates run a little higher than O'Hare. A sedan to O'Hare starts at $165, while Midway starts at $215. You can compare every route side by side on our rates page. Whichever you choose, both come with flat pricing and flight tracking.

The bottom line

If your flight works from either airport, O'Hare is usually the smoother trip from Milwaukee thanks to its position northwest of the city. But Southwest flyers and anyone with a better Midway fare should not hesitate, we make both runs flat-rate and on time. Still deciding between airports and downtown? See our Milwaukee to Chicago options too.