My wife, sons and I spent four fantastic days exploring downtown Chicago visiting museums, galleries, parks and restaurants. We anticipated a typical summer trip, but our arrival coincided with a late season cold front which brought several days of unseasonably cool weather following that initial day of rain.

Trip Planning 

CitiPass claims they save you 48%. I didn’t do the math, but that seems about right. Citipass saved us hundreds of dollars and provided perks at most of the museums including 3D movies, etc. We recommend it.

Perhaps it is a result of lingering COVID precautions or maybe it is standard crowd control practice, but several museums and galleries are regulating entry by requiring ticket holders to schedule their time of arrival. Also, I found some attractions are not open every weekday. Not understanding these facts a month ago, I procrastinated until the day before our departure to do the detailed trip planning. Honestly, I thought we could be lazy and just play it by ear, but I soon realized that wouldn’t work out to our satisfaction. I was able to use our CityPass purchase to acquire digital tickets and schedule arrival times for all four attractions which required them and kept track of this on a Google calendar ensuring nothing overlapped and there was sufficient time between attractions for dining or travel between destinations.

This was our first visit to Chicago and we knew little about the city. Normally I take time to read a history or travel guide about cities I visit before the trip so I can make informed choices. This time I didn’t have that luxury so I used Google MyMaps to create my own custom tourist destination map. Next, I determined transportation requirements to get from one attraction to the next. We used public transit, Uber and walking…lots of walking. The best deal is to buy full day or 3-day paper transit passes from the Ventra transit kiosk at the airport. We didn’t take the time to find the Ventra kiosk at the airport so we missed this opportunity. I ended up purchasing a Ventra plastic card at a Walgreen’s and loading it with a 1-day pass and some cash. Each transit trip was $2.25 per person, with transfers to 2nd or 3rd buses or trains being no additional cost for the trip. When I registered my Ventra account online I was given the opportunity to convert the $5 purchase price of the card to an equal value of transit credit. We shared the 1 card among all family members, ensuring the card was loaded with sufficient cash to cover the number of trips we’d make that day. There is a CTA app which would have been beneficial, but I made do with Google Transit (Google Maps) and the Ventra pass.

Day 1 - Saturday 

Hungry and tired from an early morning flight, we Ubered from the airport to our accomodations at the Omni Chicago Hotel, checked our bags and headed out for a hearty lunch at Giordanos’s restaurant where we enjoyed our first deep dish pizza. Reenergized, we set off walking in the light rain several blocks south crossing the Chicago river to the Architecture Center. A coworker gifted me a pair of adult passes here, so we had only to purchase a pair for the boys. We learned a bit about skyscrapers, both in Chicago and worldwide, but otherwise there was a bunch of information about climate change, energy efficiency, and building materials and techniques that we found generally uninteresting or that we already knew. So, we didn’t waste much time here and instead walked back north to the historic Chicago Water Tower where we hoped to sneak in viewing of the historical exhibits. Unfortunately, the small museum was closed.

By now the cool front had pushed east and rain was barely a drizzle so we walked east past a portion of Northwestern University to the lakefront. Turning south, we walked along the Lake Michigan shoreline down to the Navy Pier. Here we were underwhelmed, as all attractions at the Navy Pier were fee-based or - in the case of the conservatory which I was looking forward to touring - were closed for maintenance. We skipped the pricy gondola ride on the Ferris wheel. With sparse crowds likely due to the day’s rain we suspected there would be no fireworks at the pier this Saturday night so we caught an Uber back to our hotel where we ordered dinner in our room. I ran an errand to a nearby Walgreens to purchase a transit card and a few sundries.

Day 2 - Sunday 

After about 10 hours of sleep to recover from the previous day’s journey we rose and enjoyed breakfast at Sunny Side Up restaurant near our hotel. Afterwards, we caught the bus north to tour the zoo in Lincoln Park. We arrived a half hour before the gates opened so we walked about the park enjoying the beautiful landscaping.

The Lincoln Park Zoo is free of charge and we found it very enjoyable. Highlights were the gorillas, rinos, girraffes, and small mammels and primates. I don’t recall any of the bird exhibits being open, not even penguins. We suspect this for their protection due to the global outbreak of bird flu. Today was clear and cool with temperatures climbing only to the low 60s. At noon it was time to move on so we caught transit south to the Field Museum. On the walk from the transit stop to the museum in Grant Park we grabbed Chicago hotdogs for lunch from a vendor. The Field Museum was quite interesting, but given only three hours we felt rushed to see everything. We saw “Sue” the Tyrannosaurus rex skeleton, the China exhibit, Egypt exhibit and many others. We particularly enjoyed the 4D movie about octopi and, in addition to the 3D glasses, we experienced vibrations, air bursts, a wiggling vinyl string at our ankles, and microbursts of water droplets released in sync with specific scenes in the film. The sound and water drips were expected but that wiggly thing at our feet really made us jump.

Next we Ubered north to Corcoran’s Grill and Pub for a satisfying meal before walking across the street to cap off our Sunday evening at The Second City comedy club. I think our teen sons were the youngest in the audience, and the show did have a bit of naughtiness, but overall it was just silly and quite funny. We very much enjoyed all three acts. Afterwards, we returned to our hotel by Uber.

Day 3 - Monday 

Monday greeted us again with clear skies and cool temperatures which was good because we had five attractions on our list today.

Millennium Park 

We grabbed breakfast on the run from the world’s largest (3-story) Starbucks and caught a bus south to Millennium Park where we did the obligatory photos of Cloud Gate “the bean” sculpture, Buckingham Fountain and many other attractions within the park as we walked south towards the aquarium.

Shed Aquarium in Grant Park 

We were all quite impressed by the Shed Aquarium. We’ve visited Seaworld in Orlando and the Florida Aquarium in Tampa, the Aquarium of the Americas in New Orleans, and as a kid I toured Marineland in St. Augustine Florida. Chicago’s Shed aquarium’s location on the lakefront is spectacular. The view through the window wall behind the beluga whale show auditorium is just spectacular. The exhibits seem to go on forever, ranging from cold salt water to Amazon fresh. From jellyfish to tetras, sharks and rays to penguins - YES! penguins! - we had an amazing visit.

Next, we grabbed a terrific lunch from a tex-mex food truck outside the aquarium, and afterward that caught a bus north to the Art Institute.

Art Institute 

Plan for a full day here. We severely handicapped our experience at the Art Institute because we ran late from the aquarium, and then had to leave early for the next attraction. We managed to view Italian masters, Monets, some of the modern art, and some sculpture. My youngest son in particular - an artist in his own right - really enjoyed the gallery and recognized several of the contemporary artist names. Sadly, our time ran out and we nearly ran through the gallery to get out to the street to the bus stop.

Boat Tour 

We rode the bus a few more blocks north to Wendella Boat Tours at the Chicago River. The 90 minute trip traveled up (down? - they reversed the flow right?) the Chicago River, first up the north branch, and then turning around and heading down the south branch. The guide “Joe” was very personable and knowledgeable about the architecture, the architects, and engineers involved in the many spectacular buildings of downtown Chicago visible from the river. Of course there was some background history on the settlement and early expansion of the city, and of the great fire and lessons learned during the rebuilding process. We enjoyed this tour despite the fact that clouds rolled in as the boat tour got underway, temperatures dropped and the wind grew cold. This was the only time during our trip when we were uncomfortable.

After the boat tour we walked a few blocks back to our hotel to warm up, and then a few further to enjoy a dinner at Friends Sushi restaurant. The food was delicious and the atmosphere of this “shotgun” style little restaurant unique and inviting. Our sons were particularly happy with this meal.

Listen to Architect Jeanne Gang interviewed by NPR’s Scott Simon.

Sky Deck 

After the satisfying meal we were tired from a full day of activity and ready to crash at the hotel. But not so fast! - our day wasn’t done. We caught an Uber from the sushi restaurant to Willis Tower, the former Sears Tower, to get our view of the city at The Sky Deck. Fortunately, the clouds had mostly cleared allowing us a wonderful sunset and spectacular views of the city. The boys and I had no issues stepping out onto the glass flor of the Sky Deck ledge 104 floors up above the street. Meredith had reservations, but eventually did step out there briefly for our family photo. Admission allows you 3 minutes in your own sky deck (there are 5 or 6 in a row), but you are free to wander about other rooms on that top floor, all lined with floor to ceiling windows. Views were increadible all around. My only gripe is the grime…they need to use the Windex on the glass surfaces more times during each day.

Day 4 - Tuesday 

Rise and Shine! 

We slept in a bit this morning, recovering from the previous day’s activities. Then it was over for another delicious breakfast at Sunny Side Up. We realy loaded up.

Chinatown 

Afterwards, we caught the subway south to Chinatown. Ben and I did a bit of online research the night before and had made a list of things to see (and eat) in Chinatown. The boys bought keepsakes for their friends back home, and we had some sweets at a chocolatier. The authentic Chinatown on Wentworth Avenue was interesting, particularly the groceries. I was less impressed with the China-themed shopping and entertainment redevelopment project north of Archer Ave. named Chinatown Square Plaza. It didn’t seem very old, yet was already showing signs of neglect and poor maintenance. Many shops were closed on this weekday morning. Ping Tom Park was on the riverfront a bit further northwest, but we skipped it because we’d already seen it from the boat tour the evening prior.

Poor planning is to arrive in Chinatown on a full stomach, and having to leave before the next mealtime made it worse. There are so many restaurants to choose from here! But, we elected to forge ahead to the next attraction.

Museum of Science and Industry 

With sunny and cool weather we walked a few blocks to the appropriate cross streets and caught a bus east to The Museum of Science and Industry. This place is massive, and here I goofed on the schedule planning. MSI is one of the attractions requiring scheduled admission. I selected 2:00 thinking we’d have three hours to a 5:00 closing. Be advised, the MSI closes at 4:30!

We rushed and saw a lot of the major exhibits. We saw another 3D movie about deep outer space which ended putting three of us to sleep. It got a bit too abstract and theoretical during the second half. Still, we saw full size historic trains, airplanes and jets, and the German submarine captured during WW II. There was so much more to see but closing time was upon us so we walked back out to the main street and caught a bus back north to downtown.

Billy Goat Tavern 

Today we skipped lunch so after leaving MSI we were quite hungry. Arriving downtown at the river we walked down beneath street level to the original Billy Goat Tavern. Yes, this is the one upon which Saturday Night Live personalities John Belushi, Bill Murray, Gilda Radner, and Dan Aykroyd based their comedy skit “The Olympia Restaurant: Cheeseburger, Chips and Pepsi” where restaurant staff offered their patrons a limited menu.

The Goat still serves only burgers - the fried thin-patty kind - and chips - no fries - so of course we all enjoyed double cheeseburgers, chips and sodas. They hit the spot…almost. Afterwards we were craving milk shakes or ice cream. (We missed the frozen rolled ice cream in Chinatown earlier in the day.) So, we headed to Ghirardelli Chocolate Company for ice cream or shakes. This was our cap-off for our four days in Chicago.

Day 5 - Wednesday 

This morning we flew home. Unfortunately, I had a poor Uber experience where I used the reservation option to reserve a larger vehicle (XL) the evening prior to our morning ride to the airport. It confirmed, so I though all was well. The morning of departure we were packed, ready and on the curb in front of the hotel 10 minutes before the scheduled Uber pick up. Ten minutes passed and I looked at the app, seeing that the driver was 40 minutes north of the city and not moving. Clearly, he/she had stood me up. It took three more attempts to request an Uber XL that morning. Two failed because initially their ETA was shown to be just a few minutes away, but upon confirmation it reset to a half hour away. Finally, the third driver arrived with a suitable vehicle and, while we were behind schedule, we did arrive at O’Hare airport with sufficient time.

My observation is that the transportation options to/from O’Hare have not been restored since COVID. Shuttle buses to downtown are not yet operational. Our options were a pricy private SUV shuttle, inexpensive public transit train (which we didn’t want to do with luggage), or somewhat expensive Uber. The Uber XL we used was a comfortable minivan and was less expensive than the private “GO” SUV option, though only marginally after numerous fees tacked on by the City.

What We Missed 

It is no surprise that four days isn’t enough time to see all that Chicago has to offer. Attractions we missed that I had hoped to see are:

• Wrigley Field
• Soldier Field (we saw it, but tours are offered)
• Chicago Botanical Garden (up at County Line Rd.)
• Chicago History Museum
• Frank Lloyd Wright House
• A swimming beach at Lake Michigan (too chilly during our visit)
• Adler Planetarium
• Lincoln Park Conservatory (we were too early)

So, there’s plenty of reason for a return trip.