Things to Do in Chicago: Two tours and other tips

Cruise the river, admire the sights, savor the flavors of Chicago

During our last stay in Chicago (my old hometown and great place to visit any time of year) we booked two organized tours that we can definitely recommend whether it’s your first time in the city or if you’re a repeat visitor.

Looking south from Oak Street Beach to 875 N. Michigan Avenue (formerly the John Hancock building) and The Drake Hotel

Two Chicago tour recommendations

Chicago Architecture Boat Tour

I first took this tour highlighting the Windy City’s world-famous architecture many years ago when it was a fairly new offering. I loved it then and I loved it this time. Chicago has always been a great city for architecture — the old, the new, the innovative, the classic, and the beautiful blending of architectural styles.

Along the Chicago River on the Architectural Boat Tour — Marina City to the right

The 90-minute tour along the Chicago River and its branches is well worth your time. Knowledgeable guides provide interesting commentary throughout the cruise.

Skyscrapers along the Chicago River

Sit back, relax, and enjoy the views!

On the Chicago River

West Loop Food Tour – Chicago Food and City Tours

Mundialito Mexican restaurant on the West Loop Food Tour

I must admit that I didn’t know that the West Loop (former meatpacking district) was a hot culinary scene. But it is! In fact, it’s been recognized by many as one of the top culinary districts in the country along with areas like Chinatown/West Village in New York City, the French Quarter in New Orleans, and the Mission District in San Francisco. The residential and office neighborhood is vibrant and many restaurants and cafes line the streets. We loved this introduction to the restaurants and diverse cuisine of the West Loop. Our fun and interesting Chicago Food and City Tours guide took us to five restaurants — Italian, Mexican, Korean, Japanese, Roman-style pizza and a bakery for tasty desserts in jars. Make sure you arrive hungry because there is plenty to eat!

A few of the tastes on the West Loop food tour: Italian meatball, potato and pesto pizza, veggie taco & margarita, 2 Okonomiyaki dishes served with beer

It was on this tour that I learned about Okonomiyaki which is savory cabbage pancakes cooked on a griddle with a wide variety of ingredients and toppings. Totally delicious!

Sorry I don’t have more food photos — we were too busy indulging.

Other activities we enjoyed in Chicago:

Cultural activities and venues

There are countless wonderful cultural things to do in Chicago any time of year — museums (Chicago History Museum, Museum of Science and Industry, Field Museum are just of the few great ones), art galleries and museums (don’t miss the Art Institute of Chicago), nightlife, jazz and blues clubs, music festivals, art fairs, major events, concerts, recreational activities, and other cultural highlights. We missed  by a week the opening of the Obama Presidential Center on the South Side, but will definitely make it a priority next time.

Old Town Art Fair

We were glad that the annual Old Town Art Fair (held in June) would be happening while we were in the city. It takes place in the Old Town Triangle Historic District on Chicago’s North Side not far from Lincoln Park.

Food vendors at Old Town Art Fair

Old Town Art Fair

On Wells Street outside of the art fair area, there was another festival of arts going on, so we enjoyed browsing the booths and talking with artists there, too.

Artist and his glass sculptures

Art fairs are great places for finding souvenirs. I purchased a lovely hand-crafted piece of jewelry as a wearable souvenir — my favorite kind.

Buying lovely jewelry by Elizabeth Kline Designs at her booth in Old Town

Walk, walk, walk

Explore the city on foot to take in attractions like Millennium Park, walk along Michigan Avenue and the lakefront, take a break at Oak Street Beach, explore neighborhoods like Old Town (where we spent time on this trip), and admire iconic landmarks.

Millennium Park

We take time to hang out in Millennium Park (part of Grant Park) every time we come to Chicago. It’s beautiful, lively, and has frequent musical concerts, festivals, and events to enjoy. “The Bean” Cloud Gate sculpture by artist Anish Kapoor (below) is a prominent feature and a highlight for visitors.

“The Bean” Cloud Gate sculpture by artist Anish Kapoor at Millennium Park

There are two 50-ft. glass block towers at each end of the shallow pool of the Crown Fountain (one tower is shown below). It’s fun to watch the video projections of local residents on the towers.

One of two tower fountains at each end of the Crown Fountain at Millennium Park

Iconic buildings

Chicago landmark buildings — Prudential buildling and Aon Center (originally the Standard Oil Building)

The old and the new — iconic Wrigley Building and contemporary skyscraper in the background

Willis Tower (formerly Sears Tower) center building with white broadcast antennas)

Oak Street Beach

Volleyball at Oak Street Beach

Chicago’s neighborhoods 

Wells Street in Old Town

Where we stayed: Sofitel at 20 East Chestnut Street — We have stayed here several times because of its lovely accommodations, great service, and convenient location near Michigan Avenue, the lakefront, shops and restaurants of the Gold Coast. Parking tip — Although the hotel offers valet parking with unlimited in and out (no self-parking, but we knew that we would not be needing to use the car until checkout), it is pricey, so we chose to park in one of several less expensive nearby parking structures. We used the SpotHero app to make our selection and reserve our parking space and it worked out very well.

Where we ate and drank:

Restaurants

Mr. TWS at Tavern on Rush

Tavern on Rush at 1015 N Rush Street — Great place for dining al fresco and people watching. I had a petite filet mignon, Mr. TWS had seared tuna and we shared roasted asparagus.

LUXBAR at 18 E Bellevue Place — LUXBAR is a friendly and vibrant spot for great food, snacks, and cocktails. They describe the place as “the quintessential American Bar”. I had the steak frites and Mr. TWS had crab cake and salad — all delicious.

The Vig at 1527 N. Wells Street — The Vig is a 1950’s themed sports parlor. We had the best service here during this trip (and we  had good to great services in each of the places mentioned here). I had garden avocado toast, Mr. TWS enjoyed a tuna poke taco.

The Gage at 24 South Michigan Avenue — The Gage is a restaurant near Millennium Park that we try to get to every visit. I had a Caesar salad with chicken while Mr. TWS had a Nicoise salad — his favorite salad.

Beverage breaks

For drinks, the rooftop Z Bar at The Peninsula Chicago at 108 East Superior Street is a great choice, but you may have to wait for a table during busy times.

Mr. TWS sitting outside at Z Bar, the rooftop bar at the Peninsula Chicago

There are many places to stop enjoy food and drink along the Riverwalk. We stopped at the Chicago Burger Company (at the Sheraton Grand Chicago) on the Riverwalk to soak in the riverfront ambiance on a beautiful sunny day.

Enjoying a beverage along the Riverwalk

Enjoy Chicago!

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