Chicago – Walking tour from Old Town to Signature Lounge

This itinerary is about 2-3 hours long and is a really cool and delicious way for people to see some of the best parts of Chicago. Wear comfortable shoes to walk in. I’d say each person will spend $25 total for this.

This will cover breakfast, coffee, walking through Old Town and Gold Coast and ending at the Signature Lounge for lunch and drinks. You can also walk back from the Signature Lounge back through Gold Coast on an alternate route to see more mansions as well extend your outing to see one of the most realistic statues ever created of Abraham Lincoln in Lincoln Park.

1. Start at Delightful Pastries in Old Town. It’s one of the best bakeries in Chicago and were low-sugar, no preservative, organic, etc. before it was cool. The chocolate chip croissant is really good. 1710 N Wells St.

2. Walk through Old Town and head to Intelligentsia Coffee and get the best coffee you may ever have. Yes, this is a bold statement, BUT has been verified by multiple coffee-snob friends of mine. 1233 N Wells St.

3. Double-back half a block then walk east on Goethe until you reach Astor St. Make a right (south). Take the time to admire the mansions. I recommend reading about some Gold Coast history while walking on this street.

4. Make a left (east) on Division until you reach Lake Shore Dr. Make a right (south). You see less houses and stores, but it’s more direct and you get a view of the lake. This turns into Michigan Ave (Magnificent Mile), which has the best shopping in Chicago. Keep walking until you reach the John Hancock Tower, which will be on the left side of the street. Go there and head to the 96th floor, which has the Signature Lounge. Reasons why it’s better than the Sears (Willis) Tower: it’s free to go up, there’s no long waiting in line, you can eat and drink up there, and the view is better. 875 N Michigan Ave.

5. Relax and have a drink and an appetizer in one of the tallest places in the city. Fun fact: The women’s bathroom apparently has a ridiculously awesome view to the outside. Where’s my equality??

Alternate route:

  • Instead of doubling back after coffee, keep walking south and make a left (east) on Division, then a right (south) on Rush Street then a left (east) on Delaware until you reach the John Hancock Tower. You’ll see less mansions, but you’ll see more restaurants and shops.

Extended outing:

  • After the Signature Lounge, go burn off your lunch by walking back north to see more mansions and the statue of Abraham Lincoln. Go west on Delaware then make a right (north) on Rush St. Make a right (east) once you reach Division. Make a left (north) on Astor St. Keep walking north. Eventually you’ll pass a plaque on your left that describes a wooden alley. Read it and learn about its history. It helps you understand why everything burned during the Great Chicago Fire of 1871. The big house in front of it is the Bishop’s house. The Pope stays there when he visits.
  • Make a left (west) on North Blvd. You’ll pass a statue of the man who invented crowns for teeth by teaching himself dentistry. He became the chairman of Northwestern dental school, which now longer exists (unlucky coincidence lol). Once you reach Dearborn St., look to your right. There’s Lincoln.

My friends and I really enjoyed this. I hope you will too.

Here’s the map of the walk:

Chicago - Walking tour map
Chicago – Walking tour map
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