top of page


cloud gate


Chicago is one of my favorite cities in America. I always enjoy coming back, even in winter. It is a city of neighborhoods, each with its own unique culture. Wicker Park, Logan Square and Lincoln Park are all worth a visit, just to name a few. There is so much to see and do in the windy city, so if you are here for a few days (or longer), I hope my recommendations will help guide your visit.

Chicago's architecture is amazing and the best way to experience it is on an architecture boat tour along the Chicago River and Lake Michigan. Wendella Sightseeing Boats offers a 90 minute tour that floats by and provides historical information on several iconic buildings, such as the Wrigley Building and Willis Tower (still commonly referred to as Sears Tower).

For those who appreciate art, the Art Institute of Chicago is a must. It is the second largest art museum in the country and houses an impressive collection of Impressionist paintings, including works by Monet, Renoir, Seurat and Van Gogh. In the Modern Wing, you can view masterpieces by Chagall, Dali, Matisse and Picasso. Do not miss Grant Wood's American Gothic and Edward Hopper's Nighthawks. Be sure to walk the outdoor third floor bridge connecting the Art Institute to nearby Millennium Park. It offers great views of the skyline and Lake Michigan.

Millennium Park is an award winning center for art, music, architecture and landscape design. It's acclaimed features are the Jay Pritzker Pavillion, designed by Frank Gehry, the Crown Fountain and the Lurie Garden. However, the thing that has become the park's biggest draw is "the Bean" - officially titled Cloud Gate. Created by Anish Kapoor, the silver drop sculpture with its curved, reflective surface provides a fun house like mirror view of the Chicago skyline.

From the park, walk north a mile or two on Michigan Avenue up to the John Hancock Center, personally my favorite skyscraper in Chicago. Along the way you will cross the Chicago River over the DuSable Bridge (Michigan Ave Bridge) as you make your way up the Magnificent Mile. This famous section of Michigan Avenue is a collection of historic buildings, department stores and posh hotels. The Historic Water Tower is one of its most beloved Chicago landmarks. It is one of the few structures that survived the Great Chicago Fire of 1871 (Mrs O'Leary's darn cow). When you arrive at the John Hancock Center, notice its tapering shape and the massive X braces, which help stabilize its 100 stories of awesomeness. Next, jump in to North America's fastest elevators up to the 94th floor observation deck, 360 Chicago. Soaring 1,000 feet above Michigan Avenue, it offers commanding views of Chicago's lakefront, spectacular skyline and four neighboring states.

Being that I am a history buff and a fan of cool stuff, the Chicago Crime Tours is worth noting. The 90 minute bus tour takes you back to the times of Al Capone, John Dillinger, H.H. Holmes and the Chicago Black Sox. You will see the site of the Saint Valentine's Day Massacre, one of Chicago's most notorious murder scenes. You will also visit the Biograph Theater where in July of 1934 gangster John Dillinger was shot and killed by federal agents.

Staying on the North Side, whether you are a baseball fan or not, Chicago's most famous landmark just might be Wrigley Field, the ivy covered home of the Chicago Cubs. Opened in 1914, The Friendly Confines is the second oldest major league ballpark. Today, the original scoreboard is still used and is manually operated. If you are able to attend a game be sure to sit in the bleachers and sing "Take Me Out to the Ballgame" during the 7th inning stretch. After the game, check out some of the excellent sports bars around the stadium - a few of my favorites are Murphy's Bleachers and the Cubby Bear.

If you enjoy live music, Chicago arguably has the best collection of music venues in the country. From dive to classy, there are spaces for every type of music and most are operating every day of the week. Some of my favorite venues include Metro, Schubas, Double Door, Empty Bottle and Lincoln Hall. For excellent jazz in a prohibition era speakeasy atmosphere, head to Green Mill in Uptown. As far as buying music (for those of us who still do it the old fashioned way) be sure to check out Reckless Records, with 3 Chicagoland locations. One last thing to do is take a ride on the "L" (short for elevated) train for a spin around the Loop. It is quintessential Chicago at its big city best.


Chicago is a big, diverse city with a fantastic food scene. The list is endless so I'd like to share the places I always come back to and those that are genuinely Chicagoan. When you think of pizza one thing comes to mind, deep dish is king in Chicago and it is delicious. There are two choices on where to get your fix and most (some locals) will tell you it's a coin flip. Pequod's in Lincoln Park adds caramelized cheese on the crust and Lou Malnati's, with several area locations has been making handmade deep dish from scratch for decades.

When I arrive in Chicago, I must have two classics - the Chicago Dog and Italian Beef. One place offers both of the best and that place is Portillo's on Ontario Street. This timeless gangster themed food hall serves up the best greasy iconic Chicago style street food. Just remember, don't you dare put ketchup on that hot dog! Another solid institution devoted to the Italian beef Sandwich is Mr Beef. Located on Orleans Street, this workingman's favorite does an inexpensive yet impressive meat masterpiece piled with green peppers and provolone cheese.

Staying carnivorous (this is Chicago after all) you might want to visit one of the many superb steakhouses in town. For a quintessential Chicago steakhouse experience and my two favorites, head to Gibsons in Gold Coast or Gene & Georgetti in River North. With an energetic atmosphere and quality service, Gibsons on Rush Street is always a good time. For a more old school setting, Gene & Georgetti on Franklin Street has been doing massive steaks since 1941. It is not cheap, but the vibe is Chicago to the bone.

For foodies, a few of my personal favorites are The Purple Pig along with Girl & The Goat. Located on Michigan Avenues' Magnificent Mile, The Purple Pig specializes in Mediterranean small plates and charcuterie, all to be shared. With a solid wine list and some slightly eccentric dishes (pig's ear with crispy kale or roasted bone marrow with herbs) it's no wonder why they offer "cheese, swine and wine." Be prepared to wait, but it's worth it. Girl & The Goat is located in the Randolph Restaurant Corridor and serves a family style menu of tasty dishes with a global influence. The rustic decor, communal tables and open kitchen makes it a fun and lively setting. They have a long list of international wines, local craft beers and creative cocktails that go nicely with the food categories of vegetable, fish and meat. Reservations are recommended. Across the street is the best burger in town at Au Cheval and not far away is the excellent The Publican.

Heading north up to Lincoln Park, everyone must visit Stanley's Kitchen & Tap when in the windy city. This casual neighborhood joint offers up traditional American home style comfort food with a Southern twist. The fried chicken with mac 'n cheese is so choice (save Ferris). It is also a great place to drink and watch the game - you have a good chance of seeing a Chicago celebrity or two. UPDATE: tragically - Stanley's closed its doors in 2018. Also in Lincoln Park is the world renowned restaurant Alinea. This triple Michelin starred juggernaut offers multiple courses of innovative modernist cuisine. Reservations are imperative.

For the hipster in all of us, head over to Logan Square and check out the rad tiki bar Lost Lake. This stylish tropical cocktail den has an old Hollywood - island vibe, along with an adventurous drinks menu. One of several I enjoyed was called Saturn In The House Of Saturday Forever. UPDATE: Lost Lake closed down in 2022. In its place is the newly opened Common Decency. This spot has 1980s music, a glittering disco ball, solid cocktails and a colorful retro vibe.


Chicago offers many places to stay in different neighborhoods, ranging from budget to high end. In my opinion it depends on what you intend to do and more importantly, what season it is. For fall and winter months I like to be close to the Magnificent Mile on Michigan Avenue, so I stay at the Thompson Chicago in the heart of Gold Coast. This sleek hotel has modern rooms, Hi Def flat screen TVs, rainfall showerheads and free WiFi. Amenities include a stylish restaurant and complimentary car service.

If you are in town during the spring and summer months when the weather is nicer, I would recommend the Hotel Lincoln. This Lincoln Park boutique hotel has a great rooftop bar that offers stunning views of nearby Lincoln Park, Lake Michigan and the downtown skyline. There is a lobby level coffee bar, a farm to table restaurant and complimentary bike rentals to explore the neighborhood. The contemporary rooms feature flat screen TVs, iPod docks and free WiFi. Another perk with this funky vintage style property is you are not that far from Wrigleyville. With genuine people, excellent food and great sports - the city by the lake is sure to please.

bottom of page