We thought we were empty nesters when our youngest left for college. We didn’t know then that there are stages of being an empty nester.
Isabella recently moved to the Chicago after graduating from college. Just a couple of weeks later, we drove a U-Haul halfway across the U.S. to deliver her possessions.
You have to actually stop for a cross country drive to be fun!
The drive wasn’t as exciting as I had imagined. I fantasized about stopping at some interesting spots along the way. I envisioned a mini cross country adventure. That didn’t happen.
However, I am a delighted and proud mother hen. Isabella whisked us through the City of Chicago on a perfectly planned and executed 1-day itinerary two days after our delivery!
There Are Several Lovely Towns West of Downtown Chicago within Easy Train Access.
Our point of delivery was about 30 minutes west of downtown Chicago, Wheaton, Illinois. We carved out one day into the two and a half days that we were in the area to spend in downtown Chicago. We had about 9 hours on a Saturday afternoon and evening to pack in as much as we could during our visit to the City.
WARNING: If you don’t like walking, and sometimes fast, you won’t like this itinerary.
TRAVEL TIP: Wheaton is on the Metra line and about 50 minutes, either by train or driving (due to traffic), from downtown Chicago. There are several train stops between Wheaton and the Chicago OTC station, including towns like Glen Ellyn, Lombard, Villa Park and Elmhurst. Any one of these towns may be a convenient and economical place to stay outside of downtown Chicago.
The First Thing To Do in Chicago is to Visit Millennium Park.
Total Time To Allot: 30-45 minutes to see a couple of the highlights.
We started our day with a stop at Millennium Park located in the Chicago Loop area. The park is on the east side of the downtown area. Chicago shines bright on a sunny day. Glass skyscrapers crowding the horizon and shooting up around you glimmer so bright they are almost blinding in the sunlight. Millennium Park is beautifully landscaped with flowers and trees. It is a garden sanctuary in the middle of the glass city.
HOT TIP: We drove into the City and parked in the Grant Park North Garage. The garage is located right across the street from Millennium Park. The garage entrance is at 25 Michigan Avenue.
HOTTER TIP: Our millennial escorts used the parking app, SpotHero, to find a parking spot and reserve our parking space in advance. You pay when you leave the garage by scanning the app on your smartphone. Never would we have figured that on our own!
Take 5 Minutes to Take In Crown Fountain.
In the mid-afternoon on a sunny second day of summer, Millennium Park was packed with people. The first thing we encountered in Millennium Park, other than the crowds, was Crown Fountain. There are two huge panels souring up out of the concrete. The panels project images of human faces. Interestingly, the collection of faces shown are the images of 1000 Chicago residents. The faces are meant to reflect the varied population of the City. Waterfalls flow down the panels. Fountains sprinkle and spray intermittently from them providing relief from the heat on a hot summer day.
Expect Some Wind In the Chicago Summer, and Bring a Light Jacket.
Honestly, it is hard to imagine ever being too hot in Chicago. It was the end of June when we visited. The temperature was in the 80’s. Yet, true to it’s name, the Windy City was still windy. Warm and cool breezes washed over us as we toured the City. We never felt hot. I kept taking my denim jacket on and off.
Spend 10 Minutes for Photo Ops at The Chicago Bean.
The famous Chicago Bean is also known as “Cloud Gate.” You can find your way from Crown Fountain to The Bean quite easily. Follow the crowds. This trip was out of the ordinary for us. We did no research. We had no plan. We just followed Isabella around her new city. Pat had never heard of The Bean.
What is The Bean?
The Bean is a polished stainless steel structure 66 feet long and 33 feet high. Obviously, it is shaped like a bean. The concave part of the bean forms kind of an arch for visitors to walk under. The high shine and shape of The Bean make it like a carnival mirror reflecting distorted images. At the same time, at various vantage points The Beans seems to perfectly reflect the Chicago skyline. The design of The Bean is inspired by liquid mercury.
HOT TIP: Be sure to inspect The Bean from all sides. Each provides a different perspective.
When we were making our way to the Chicago Bean, Pat asked, “What’s The Bean.” When we found it, he started calling it “The Egg.” It stuck. Even after I corrected him several times, eyes rolling, of course, to Pat The Bean is and probably always will be, The Egg.
Expect Crowds When You Visit The Chicago Bean.
Like any other tourist attraction, The Bean was crowded with throngs and groups of people, including a wedding party and a quinceañera! Notwithstanding the number of visitors, people were relatively polite. It was pretty easy to create a space for a photo opp near The Bean. People generously volunteered to snap group photos.
Distance Approx. 1.4 miles (about 30-45 minute walk).
We are fast walkers. We chose a route from Millennium Park to Navy Pier along North Columbus Drive and over the Chicago River. It took us about 45 minutes to get to Navy Pier due to a short detour. At the N. Colombus bridge there are beautiful views of the river against the back drop of the Trump Tower and the surrounding skyscrapers. There we stopped to take the stairs down to the Riverwalk for a quick sneak peak before proceeding to Navy Pier.
The inviting, lovely blue-green color of the Chicago River were surprising. It reminded me of photos of picturesque mountain lakes on Instagram. On the Riverwalk and at Navy Pier, the vibe was full-on summer celebration. Tour boats crowded with people, yachts, kayaks and all kinds of watercraft cluttered the River. Everyone on the boats clearly was having a boat load of fun! It was disappointing that we didn’t have the time to enjoy a boat tour.
There were a lot of slow walkers along our route to Navy Pier. As we got closer to the Pier the crowds got thicker. The atmosphere grew a little more carnival like. Balloons and bubbles floated through the air and rickshaw drivers hawked their rides. We happened to be at the Navy Pier during the Chi-Soul Fest celebrating Chicago’s legacy of soul. During our 2-hour stop at Navy Pier we saw DJ’s and musicians all along the Pier playing soul music from the 1960’s through today.
Approx. Time To Spend – 2 Hours.
The energy and activity on Navy Pier were unexpected. I knew nothing about The Pier before we visited. All I anticipated was a long walk-able pier with cool views. What we found on Navy Pier was a pleasant surprise. There are so many interesting facts and things to do on Navy Pier that I could write a whole blog post on that topic alone. You can find more information on the Navy Pier website, of course.
Here are some highlights:
- Strolling to the end of Navy Pier you will catch breathtaking views of the Chicago skyline along the shoreline of Lake Michigan.
- Navy Pier is just over a half mile long.
- The Pier is lined with restaurants, bars, cafes and tourist attractions, like boat excursions, tours, and boat rides.
- You will find an amusement park about mid-way up the Pier with various rides including a magnificent, nearly 200-foot Ferris wheel.
- Millions of people visit Navy Pier each year.
We spent about two hours on Navy Pier. You could definitely spend the bulk of a day. The walk down the Pier involves a lot of tourist dodging. This is especially true if you are on a mission to cover as much territory as you can in a short time.
I wouldn’t miss walking the entire length to the end. The crowds seem to thin the farther down the Pier you travel. When you reach the tip, you will be rewarded by an almost 360 degree view of the massive Lake Michigan. It seems like an ocean.
As well, you will enjoy panoramic views of the City. An over-sized anchor rises from the end of the Pier, presenting another selfie spot in this photogenic city. I imagine that this is a perfect spot for a rest stop to take in the views for a bit longer than we did. In the few moments that we did hesitate after snapping a pic, we were impressed by the passing sailboats, a tall ship, and even a Chicago Fire Department boat!
Secretly, Pat and I are devout fans of all three Chicago TV shows — Chicago Fire, Chicago PD and Chicago Med. We half expected to run into Kelly Severide and Matt Casey somewhere in the City. When passing by a fire station, we were tempted to just wander in (as people do on the show) to find Otis and Mouch sitting around.
After almost running from Millennium Park to Navy Pier, and dodging tourists like an NFL quarterback, you are going to need a rest and probably a drink. The running part is a bit of an exaggeration. However, you should definitely refuel to be ready for the rest of the itinerary.
Make A Worthwhile Stop at Offshore Rooftop Bar.
We fortuitously landed at Offshore. Offshore is a sprawling rooftop bar/restaurant located near the end of the Pier. It was a lucky roll of the dice. We highly recommend Offshore for a snack and a drink, or two. The views of Chicago and Lake Michigan alone are enough to make this a worthy stop. With its all white decor and glass windows, Offshore seems to blend into the lake. It’s a hip spot with huge outdoor areas, fire pits, game areas, pool tables and inside lounging areas. Our photos don’t even begin to do it justice.
Try A Signature Cocktail At OffShore.
It was difficult to chose a cocktail from Offshore’s fun signature drink menu. I was tempted to go with “Secure the Bag” just because it was pretty and cute, which are usually bad reasons for decisions. The fruit punch colored Secure the Bag comes in a pouch with a straw like the Capri Sun juice bags that I used to pack my kids for lunch.
I settled on a more sophisticated margarita. Instead of the traditional margarita glass, it was beautifully presented in a clear lowball glass. It had a distinctly smoky flavor and was adorned with an edible violet flower floating on top.
Portions are Huge on the Offshore Sharing Menu.
The portions on the sharing menu are extra large! All four of us were satisfied with an order of shoestring potato stack (fries) and chicken taquitos. Offshore is trendy, cool and fun. It is the type of place you may find on a swank Caribbean island like St. Barts, or in the New York Hamptons.
What to Do Next in Chicago – Hit The Riverwalk for More Action.
Approx. 1.25 Miles to The Riverwalk. Plan for 1 hour or so.
After recharging on Navy Pier, you’ll be ready for more sightseeing on foot. From Navy Pier, head back toward the Chicago River because your next experience will be the Riverwalk. Find directions here.
quick FACTS ABOUT THE CHICAGO RIVERWALK:
- The Riverwalk is 1.25 miles, spanning from Lake Michigan west to Franklin Street.
- There are six coves of the Riverwalk–the Marina, the Cove, the River Theatre, the Plaza, the Jetty and the Boardwalk.
- There are plenty of places to drink and dine into the evening on the Riverwalk . It may be THE perfect location to enjoy a romantic evening in Chicago.
- An emphasis of the Riverwalk is recreational experiences. Among them are kayak tours, River cruises, dinner cruises, party boats, and people watching at the many riverfront establishments.
- There are over 500 works of public art on the Riverwalk.
Walking from the Lake Inland, the Excitement Grew.
As we progressed, the venues seemed to become more trendy and definitely more popular and populated. Like Paris, France the seating was situated for the best people watching — facing out toward the promenade. Everywhere the crowds sat looking toward the river, watching the spectacle of island party boats, water taxis, and yachts with bikini clad women dancing to loud music cruise by. Maybe I’m getting old, or maybe it’s a Chicago thing. But, it seemed way too cold to be flaunting a bikini on a boat in the Windy City in late June.
Boats!
We were equally surprised by what we found on the Riverwalk as Navy Pier! I don’t even remember hearing about the Riverwalk on my previous visits to Chicago. I guess it’s been a long time since my last visit. Walking west on the Riverwalk, each bar/restaurant seemed more inviting than the next. There was outdoor seating, games like the ever-popular cornhole, cold drinks, and crowds! You will also find the McCormick Bridgehouse and Chicago River Museum on the Riverwalk. Also like Navy Pier, you could spend a good part of a day exploring the Riverwalk.
Find the Action at the State Street Area on the Chicago Riverwalk.
The area near the State Street bridge seemed to be the most happening. City Winery and Tiny Tapp on the south side of the River looked like a trendy spot to park yourself. It was packed with people who were people-watching, hanging their legs over the edge of the patio.
Sitting at City Winery the view across the River is of extravagant boat slips constructed under two oddly configured towers sticking out amid the sophisticated Chicago skyline. These buildings are formally named the Marina Towers. They are aptly nicknamed the Corn Cob Buildings. That is exactly what they look like – hollowed out and a little bit spooky corn cobs.
The scene on the north side of the River seems like a scene right out of a James Bond movie. You can easily imagine Bond jumping, or falling, out of a window from the sophisticated Smith & Wolensky restaurant hanging over the River. He lands with a perfect roll onto a yacht below that speeds off down the Chicago River out of the sight as well as the grasp of some evil antagonist.
Check Out the Loop Bridges Along the Riverwalk.
We have never been to Venice. But the blue green Chicago River winding through the City under movable bridges looks a little like photos and movies scenes of Venice. All that seems to be missing are the gondolas with singing gondoliers. There are 18 “Chicago Loop Bridges.” You will find these movable bridges over a two-mile stretch in the downtown Chicago loop. At the beginning and end of the boating season all of the bridges are lifted to allow boats to pass from the River to Lake Michigan.
Fear Not! After the Riverwalk, There’s Time for Another Pit Stop.
At the end of your stroll along the Riverwalk, you will be a about half way through your day. You may be slowing down a little by this time. Our stroll along the Riverwalk was a bit more leisurely than our quick paced walk from the Navy Pier. It was warmer as we walked west and away from Lake Michigan. I definitely broke a sweat and worked up a thirst as well as an appetite.
After The Riverwalk, Go To Roof on theWit.
Time to Allot 1-1.5 hours
You next stop is a rooftop bar, called “Roof on theWit.” It is an ultra cool spot to get your swank on. Unexpectedly, the trendy theWit hotel is a Double Tree. It’s located on North State Street in downtown Chicago. When the elevator doors open on the 27th floor, you have arrived at Roof. We had reservations for 6:00 p.m. for drinks. Yes, I said, “reservations for drinks.”
Reservations are Required, Even for Just Drinks at Roof.
Secretly, I thought Isabella, like her mother, had over planned the day with a happy hour reservation. That definitely was not the case. I have since discovered that Roof is internationally acclaimed. In 2018, Roof was rated one of the top three rooftop bars in the world by Travel & Leisure!
We announced our reservation to the hostess, who was playing linebacker at the same time. She was literally blocking people from entering the bar/lounge and inquiring if they had a reservation. Still, I thought, she must mean for dinner. I was wrong again. The hostess escorted us around a decorative panel into the bar area and to our reserved low sofas situated for conversation around a low table. She shooed away the other patrons sitting there, apparently without reservations. And, we sat. Without a reservation, your only option is to stand at the bar.
The Views from Roof Are Incredible.
Floor to ceiling glass at Roof provides sweeping views of the Chicago skyscrapers looming close by. They will take your breath away. A DJ spinning house music tops off the cool, laid-back vibe.
Consider Making Reservations for the Rose Garden.
An outdoor area dubbed “the hangover,” presumably because it “hangs” above the City, is a gorgeous, classy and romantic “rose garden.” To experience the rose´ wine served up in the rose garden along with the glorious views of the City, you will not require rose-colored glasses. You just need special reservations.
The wood-fired pizzas at Roof look very tempting . However, your time is short in this cool City, Chicago. Don’t ruin your dinner appetite at Roof on this visit. You will want to experience one more spot before your nine-hour Chicago adventure ends!
Take a Stroll Down Michigan and North Wabash Avenues.
Distance Approximately .75 miles. Time to Allot-half hour to Walk to 696 North State Street to Quartino Ristorante & Wine Bar.
From North State Street we headed to the famed Michigan Avenue for a stroll. It was early Saturday evening. Starting a few blocks north of East Randolph Street, by this time of day it seemed like we missed the best of the Magnificent Mile. There was not much activity or much to see. nWe were running out of time before or dinner reservation. We decided to backtrack toward our almost final destination, Quartino Ristorante & Bar.
North Wabash At Dusk Is Quite Magical.
North Wabash Ave 
We took a turn onto North Wabash Avenue, also known as Jeweler’s Row. The Loop, nicknamed “The L”, is the elevated rail system that loops around Chicago’s downtown area. The east branch runs along N. Wabash. Walking along the uncrowded street at dusk as the street lights flickered on was surreal. There were few pedestrians. We barely noticed the rattle of The L. Instead, we were mesmerized by the soft sunlit golden glow of the skyscrapers peeking out at the end of the street. We continued on to 626 N. State Street. You can follow our route here.
Dinner At Quartino is a Solid Choice.
Time to Allot for Dinner-2 hours.
If you decide to follow our route and go to Quartino Ristorante & Wine Bar for dinner, the leisurely stroll from Roof is short in distance and time. Isabella reserved an outdoor table for four for dinner because we love uncomplicated Italian food in a friendly atmosphere. That is exactly what we found.
Quartino’s website describes the place as a bustling downtown Chicago restaurant. “Where wine is cheaper than water,” they say. If you are intent on having dinner at Quartino, you must make reservations! It was packed. Inside the restaurant it was wall to wall people. It was loud and lively. Diners chatted amid the subway tile, worn wood, rustic metal restaurant. Glasses and plates clanked loudly. Sounds from the open kitchen and the bar area joined the cacophony. We lucked out in scoring a table on the outdoor patio area along the street. At that location, the dining experience was a bit more peaceful. Plus, we had front row seats at the scene parading in and out of the joint.
Seriously, the Wine is Cheaper than Water.
It’s true! The wine is cheaper than water at Quartino. A bottle of Pinot Grigio at Quartino cost only eighteen bucks. The restaurant specializes in Italian small plates to share and Neopolitan thin-crust pizza. The small plates are really more like moderately size plates, rather than the huge plates often found an old-fashioned Italian restaurants. The pizza requires a forty-minute wait for cooking. We each had our own plates and were pleasantly satisfied. The prices were relatively inexpensive. Quartino is definitely a delightful and solid choice for an Italian meal in downtown Chicago. If you plan on eating inside, be prepared for a cacophonous atmosphere!
Hands Down Our Favorite Experience was the Willis Tower.
Time to Allot-Approximately 1 Hour.
tip: arriving at willis tower close to 10:00 p.m. there were no crowds. hours vary depending on the time of year.
Our bellies were full of bread, pasta, wine and warm chocolate brownies to die for! Our feet and legs were exhausted. We decided to give ourselves a break and opted for an Uber to our final stop — the Skydeck Chicago at Willis Tower. If you chose to walk from Quartino, it’s only about 1.4 miles southwest. The walking route is here.
a few FUN FACTS ABOUT THE WILLIS TOWER
- The 2nd tallest building in the western hemisphere.
- There are 103 floors in Willis Tower.
- On the 103rd floor is a glass viewing platform, known as “The Ledge,” the highest public viewing area in the U.S.
- On a clear day you can see 4 states, Illinois, Indiana, Wisconsin and Michigan
- The building sways from an average of 6 inches up to 3 feet!
The Elevator Rides to the Ledge Provide Preliminary Thrills.
We purchased Saturday night special tickets in advance, online for $20.00 per person. We arrived at around 10:00 p.m. At that time of evening, there were no lines to the elevator that whisks you to the 27th floor. That first elevetor is an experience in an of itself. The next elevator ride to the top is narrated, providing a brief history and quick facts about the Tower and the elevator. It felt like the elevator was swaying as we ascended. I enjoy amusement park rides. But as we rose, I felt my stomach drop. I watched one of the members of our group turn ghost white. I was concerned that he might faint!
Views from The Ledge Are Remarkable!
At the top, we waited only a short time — maybe 15 minutes — for our turn to step out onto the glass Ledge.
I expected the entire 103rd floor, or at least a large part of it, to have a glass floor. However, there are actually three glass ledges with floor to ceiling windows. The glass Ledges jut out of one side of the top floor of the Willis Tower. Glass floors, walls and a ceiling enable viewing in all directions. While waiting for your turn on the Ledge, video screens hanging on the walls encourage you to take unique photos and tag them @willistower on Instagram. An attendant standing just outside of the glass Ledge ensures that visitors don’t monopolize the view.
I couldn’t help but catch my breath when I stepped out onto the glass. In all of our travels, we had no other experience like this one. It felt as if we were viewing Chicago hanging high above the City in space. I was thrilled that our visit was in the dark of night. The City lights sparkled and twinkled against a black star speckled sky. The skyscrapers were like Christmas trees growing out of the dark. The headlights on cars travelling in one direction formed an illuminated white line in one direction. The tail lights of vehicles travelling in the opposite direction created a lit red streak parallel to the white. We couldn’t get too creative with our pose. We didn’t want to risk the rolling eyes and embarrassment of 20-something Isabella.
Don’t miss Willis Tower. And, I think that the dramatic view at night makes evening an ideal time to visit. Our visit to the Willis Tower was the whipped cream and the cherry on top of the delectable, delightful day in Chicago.
Chicago is a city much less intense and overwhelming than larger cities like Manhattan. The streets were not jammed with traffic, nor was noise and pollution oppressive. Throughout downtown Chicago you will find huge lush flower pots and places to sit and relax. There is enough to see and do in Chicago to consume several days. Yet, you can cover a lot of ground in just one day.
Now we are legit empty nesters, I think. Our travels will continue, but things seem different. Now it really feels like it’s just the two of us. It is bittersweet. I am sad that Isabella flew so far from our nest. But, I am also happy and proud that she is spreading her wings. I am thrilled that Isabella loves travel and exploration, like we do. Of course, I am also elated to have a reason to frequently visit and explore the Midwest, and especially the lovely city of Chicago.
