Chicago is on everyone’s bucket list. And it’s easy to see why. With a picturesque shoreline, exciting history, and a vibrant culture, there’s something for everyone. Whether you’ve got an extra day, down time on your tour, or space between sporting events, we’d love to help you explore Chicago’s secrets.

And, if you’re familiar with the area, maybe you’ll find somewhere new to explore the next time you decide to play hooky.

A Morning of Chicago’s Secrets

A morning visit to the Driehaus Museum, 40 E. Erie Street, lets you step into one of Gilded Age’s grandest mansions. From the ground up, all three stories of the 1878 residence offer a sense of the past.

And, don’t forget to check out the servants’ quarters, too!

All of the museum’s rooms contain some of the original furniture, a large collection of Tiffany glass, and items from the 1983 Chicago World’s Fair.  One of the Tiffany lamps, originally $550, is now priceless and may inspire you to mine your attic for overlooked treasures.

For Lunch – More Than Just a Hotdog

A Chicago hotdog is a must for lunch.

But you don’t have to buy one from a street vendor and drip mustard and relish on your shirt. Try a gourmet hotdog at the Four Seasons Hotel’s Allium Restaurant. Although the menu chances according to produce in season, their staple is their hotdog. And, the hot dogs, the poppy-seed buns, and all the condiments are from the Allium’s chef’s kitchen.

Catsup on a Chicago hotdog is anathema, but the fries, served in a brown paper bag, are served with one of the chef’s creations: tangy balsamic catsup. The restaurant has a gracious décor, probably the finest place you will ever enjoy a hot dog.

Afternoon – Culture for All

An afternoon visit to the 150-year-old Chicago History Museum, highlights Chicago’s growth from a small fort to a world-class city. Dioramas display dramatic scenes from the 1871 fire that was not started by a cow owned by Mrs. O’Leary.

A five-foot cardboard cutout displays what a Chicago hotdog should look like and contain. Artifacts include toys, clothing, and appliances from days gone by and recreated shop windows from now-defunct department stores.

And, you can sit in one of the earliest L trains.

Chicago at Night

Dinner at Maxwells at the Club is always tasty and known for its Jewish food. On Wednesdays, they offer their small plates specials, both cold dishes and hot. Try the lamb koftas with pine nuts and don’t miss their fried artichokes. You can ask for a dessert sampler to share as it is difficult to pick just one of their outstanding desserts.

Evenings in Chicago often involve the theater.

But, expensive, well-known theaters and performances are not the only options.

For other options, see what’s playing at the Shakespeare Theater on Navy Pier. It is not always Shakespeare.

The Looking Glass Theater favors original shows and contemporary adaptations of classic books and plays. This intimate theater is housed in the historic Water Tower Water Works.

And, the 800-seat Music Box Theater shows independent, classic, cult, and foreign films. This old gem of a theater goes back to 1929 and is one of Chicago’s little secrets.

This custom tour gives you time to explore Chicago.
So what are you waiting for? Let’s book now!