Subway to Drake Hotel

Question

Wedding this weekend.

Some of our party is flying in from Midway and others are flying in from Ohare.

Some would rather use mass transit rather than Uber, but it looks like that might not be the most reasonable thing to do. Looks like at least from Ohare, it involves switching trains, walking with luggage, etc.

Midway seems to be direct, but still a 20 minute walk to the Drake.

Any advice?

Answer

Traveling from Chicago’s airports to the Drake Hotel via public transit is possible, but there are differences depending on whether your party is coming from O’Hare or Midway, and some practical considerations to keep in mind.

From O’Hare: The “L” Blue Line offers a direct train to downtown, but it will require at least one transfer to reach the Drake Hotel near the Magnificent Mile. Specifically, you can take the Blue Line to Washington station, then transfer to the Red Line (or walk east) toward the Grand/Michigan area. The total trip with luggage and walking can easily take 45–60 minutes, depending on wait times and crowding. Navigating escalators and stairs with luggage can be cumbersome.

From Midway: The Orange Line goes to downtown without requiring a transfer. You can get off at the State/Lake or Adams/Wabash stations and walk north along Michigan Avenue to the Drake Hotel. Expect about a 20-minute walk from the station, which can be manageable if you have small luggage, but challenging if your bags are heavy.

Here are some practical options to consider:

CTA + Walking: Economical option, works best with light luggage and if travelers are comfortable navigating trains and stairs. From Midway, it’s more straightforward; from O’Hare, expect transfers and a longer journey.
Airport Shuttle: Services like Go Airport Express or hotel-arranged shuttles can drop you closer to the hotel door. Slightly more expensive than transit, but more convenient with luggage.
Uber/Lyft or Taxi: Fastest and most direct, especially for O’Hare travelers. Expect ~30–45 minutes from O’Hare and 20–30 minutes from Midway, depending on traffic. Cost varies from $35–$50 from Midway, $50–$70 from O’Hare.
Combination: From Midway, take the Orange Line; from O’Hare, consider Uber or taxi unless your group is comfortable with public transit and luggage management.

Summary: For convenience, especially with luggage, O’Hare travelers are generally better off taking a taxi or ride-share. Midway travelers could reasonably use the Orange Line and walk, though luggage weight and weather should be considered. If minimizing cost is a priority, public transit works, but it’s not the easiest for first-time visitors with heavy bags.