Video – ORD Layover Excursion: a 6-Hour Tour of Chicago

A long layover can be an impromptu vacation or a mind-numbing marathon of CNN Airport Network shows. Inspired by my own 5-hour layover excursion through Frankfurt, I grabbed my iPhone and shot what I’d recommend you do and see on a long layover at O’Hare Airport.

Using foot power and a one-day unlimited pass on Chicago’s ‘L” (subway/metro), this tour hits:

Here’s a map highlighting each stop on the tour:

View ORD Layover Excursion in a larger map


Some ideas on how you can customize this tour…

  • If you’re coming in from Midway Airport, take the CTA Orange Line to the Loop’s Clark/Lake Exit to pick up the Brown Line north. Midway is closer to the Loop, so you can shave 40-60 minutes off the itinerary
  • You can save about 30 minutes by taking a taxi to Wrigley Field from O’Hare. You can then pick up the itinerary heading south from the Addison ‘L’ stop
  • If you’re interested in high-end shopping, take a left (east) at North Ave (instead of the suggested right), right (south) on State Pkwy, bear left at Rush St, and then turn left (east) on Oak St. Shop along here to Michigan Ave and head south (right). Get a beer/glass of wine at the bar on the 96th floor of the John Hancock building and enjoy the view. When you’re finished, take a taxi to Daley Plaza and pick up the itinerary there.
  • If you want to go to the top of the Sears Tower (no Chicagoan calls it the Willis Tower), keep heading across the Loop (west) on Adams after the Art Institute. Take a left (south) on Franklin one block to Jackson for the entrance to the SkyDeck.
If you have any other suggestions or your experience doing this tour, please leave a comment here.

4 comments on “Video – ORD Layover Excursion: a 6-Hour Tour of Chicago

  1. Jeanette Irwin says:

    Great idea for a video series! I’ve often wanted to take advantage of long layovers by making a quick trip into the city the airport in, but have never been able to figure out what to do with my luggage (if I can help it, I don’t check my bag, but bring it on the plane with me). Do you have this issues as well, Mark? If so, what do you do about it?

  2. mark says:

    Jeanette –

    With increased post-9/11 security, short-term luggage checks are scarce if not extinct in the US and increasingly expensive in places like Heathrow. While I carry-on almost exclusively, I’ll check my bag if I’m doing a layover tour (I did this for my Frankfurt sprint). If it’s a more spontaneous excursion, I’ll try to check my bag at a hotel at the airport or on my first stop. I’m usually successful, but I also generously tip to help grease the skids.

  3. Frick says:

    Great video, it seems my layovers are never long enough to pull off any excursions. I’ve watched the Wiener Circe show on Tru TV, wow it’s much calmer during the daylight hours. I was looking at your Flickr pictures, take a look back at your My Briefcase picture from 2006 technology certainly has evolved in the last 7 years.

  4. mark says:

    Steve –

    I lived around the corner from the Wiener Circle in my single days. I can tell you from personal experience that it is a very interesting/entertaining place after midnight on Friday or Saturday.

    I was looking at that old briefcase picture the other day. The Moto clamshell phone and Bluetooth headset are the standouts, though the old U2 clickwheel iPod certainly has a vintage feel to it.

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