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Between the two, O'Hare is definitely the better choice. Depending on traffic conditions, the drive from O'Hare to Great Lakes can be anywhere from 40 to 80+ minutes. In the absolute best circumstances, it would be at least an hour from Midway, and standard rush-hour traffic snarls could push that to well over 2 hours.
Another alternative to consider would be to fly to General Mitchell Airport (Milwaukee's big airport). Traffic is consistently better on the I-94 corridor south out of Milwaukee than north out of Chicago; the drive would take you about 50 minutes. Unfortunately, it may be difficult finding non-stop rates to Milwaukee that are competitive to non-stop rates to O'Hare.
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