My Kind of Town: How to Spend a Long Weekend in Chicago

A mother/son morning walk from The Peninsula Hotel down to the waterfront with coffee from Pierrot Gourmet.

I worked for a Chicago based company for several years so have spent a fair amount of time there but have a new reason to visit now that my stepson recently moved to the windy city to live and start his first job after graduating from college. We’ve visited him twice now and have had the best time exploring the city and all it has to offer.

Chicago is a great city to visit if you’re looking to have a fun, active weekend with your family. It is easy to get to (one hour, direct flight from where I live in Birmingham, Alabama), it is very walkable (despite the headlines, we had no issues whatsover with crime or feeling unsafe), the food is great (LOTS of Italian), there’s architecture, history, a beautiful art museum, sports, etc.

Plenty of activity to fill a weekend but not so much that you feel like you have to hit the ground running at 7 AM. And by the way, people from Chicago LOVE their town. Everyone from our bike tour guide to the concierge to the waiters at our restaurants were so enthusiastic about showing off their town to us.

Here are some suggestions in case you are looking to spend a long weekend in Chicago soon. -and please share!

STAY

St. Regis – very modern, new, upscale hotel. Great location overlooking the river.
Four Seasons – typical Four Seasons 10/10, we enjoyed the hotel bar before going out to dinner.
Peninsula – not my favorite hotel chain, but this one in Chicago is in a great location and was perfect for our long weekend stay. My son thoroughly enjoyed the indoor pool and hot tub after a long day of sightseeing.

I’ve stayed at all three of these hotels and they are all great for different reasons but here are my honest thoughts having experienced them all. The St. Regis is new and modern; has beautiful water views. Full disclosure – I did find this hotel to be a little on the chaotic side, but it was likely because we were staying there over Labor Day weekend. The Yankees were in town and the entire team stayed at the hotel, which was cool, but it also meant lots of security, fans standing in line outside to see the players, etc. (by product of that, being asked every time we came in if we were in fact guests of the hotel.)

Basically, I thought they took themselves way too seriously and I wanted to tell them to knock it off, we aren’t in LA.

There were also several big events going on so it was very crowded with people coming in and out of the hotel all weekend. Our rooms were very nice – & you cannot beat the views from the hotel rooftop – but overall, I think I preferred the quieter Peninsula and Four Seasons.

The Peninsula is an older hotel but very well maintained and you can’t beat the location – my son and I walked to the waterfront, Giardano’s is across the street and the restaurant at the bottom of the hotel has an incredible breakfast (even if you aren’t staying at the Peninsula, you have to go and order the cinnamon roll. See below if you need convincing.)

EAT:

Pizza! Deep dish, of course – we’ve eaten at both Gino’s and Giordano’s – both are great; slight preference to Giordano’s because their seating and ordering system is efficient. Pizano’s is also a great choice with several locations.
Pizzeria Portofino – pizzas, salads, seafood on the waterfront
Ralph Lauren RL Chicago – I love this restaurant for dinner – martinis, oysters, pigs in a blanket and other Americana fare. Also a really great spot for lunch.
Bavette’s Steakhouse – DELICIOUS steakhouse restaurant; make reservations far in advance
Gibson’s Bar & Steakhouse – old school Chicago steakhouse. Chaotic (in a good way), fun atmosphere and the food is great.
Hugo’s Frog Bar & Fish House – sister restaurant and next door to Gibson’s, seafood focus vs steaks but they have those as well.
Smith and Wollensky’s – patio dining; we ended up going here for lunch on our last visit right after our bike tour. It was great being able to sit on the patio on a beautiful sunny day and enjoy a well deserved beer with lunch.
Pierrot Gourmet – a must for breakfast; get a cinnamon roll! At the bottom of the Peninsula Hotel and around the corner from RL restaurant.
Volare – Italian; great variety of pasta, pizza, seafood, steaks etc.
Piccolo Sogno – another Italian spot with outdoor seating. It was a little chilly when we were there but we sat outside under the heaters and it was perfect. I loved everything we ordered.
Billy Goat Tavern – our tour guide recommended; greasy spoon spot serving burgers and beer, go to the original location on North Michigan Avenue (lower level)
Timothy O’Tooles – the perfect spot if you’re in need of a place to watch college football

Yes they have a photographer that walks around and takes your photo and sells it to you for a small fortune.

DO:

Bobby’s Bike Hike – Cannot recommend this experience enough; we opted for the private version with e-bikes. You can cover so much ground on this tour – everything from Millennium Park and the iconic “Cloud Gate”, a.k.a. “bean”, along the waterfront (both the river and Lake Michigan) great views of the the architecture and more. It is one of my favorite city bike tours ever – I have actually done it twice on both visits. Great for adults and kids alike.
Architectural Tour River Cruise – we used the “First Lady” company at the recommendation of our hotel concierge and opted for the skip the line/priority boarding tickets (you will not regret it – lines are long and these tickets allow you to board early/first and pick your seats). Good to know: although the tour is really wonderful and interesting, be aware that it is 90 minutes long in case you have younger children or adults that have short attention spans! On the positive side, there’s a full bar on the boat. 🙂
Art Institute of Chicago – My art loving son and I visited the art museum while the other boys were watching endless hours of football. I have mentioned this on Instagram but if you haven’t already, definitely download the Bloomberg Connects app – it is so cool. You need your wireless headphones but basically this app provides free guided tours and background information for “cultural destinations across the globe”, over 1200 in all. All you do is download the app, find the museum you’re visiting, navigate the information to find what you want to see and go from there. I have used it at the Guggenheim, the Frick, and the Art Institute for Chicago – so easy and convenient.
Willis Tower, formerly Sears Tower Skydeck – There is nothing more Chicago than this experierence; also purchase the timed tickets to skip the line (103 floors high)
Frank Lloyd Wright Home & Studio – for the FLW fans, the home that Wright bought at age 22, redesigned and lived in for most of his career is located about 30 minutes outside the city of Chicago in Oak Park, Illinois. My son and I took an uber and took the tour of the house and his studio. I really enjoyed it as did my son, but you have to be into architecture and design to enjoy it I think – otherwise you might find it boring but for the design enthusiasts the tour is very interesting. They have a great group of dedicated volunteers and FLW historians who offer the timed tours for a small fee.
For the littles: Museum of Ice Cream and Sloomoo Institute, a.k.a. Slime Museum
Baseball Game – Cubs or White Sox – The Cubs were not in town when we were there so we opted for a White Sox game instead (playing the aforementioned Yankees who were staying at our hotel). It was not quite as fancy as the Cubs experience but checked the box – we left halfway through and went out for pizza. Having been to both, I would say go to a Cubs game if you can – it is a great experience for any sports fan.
Navy Pier – This is a big tourist attraction in the city, but for some reason we did not visit on either of our trips. I think it has more for little children to do vs. teenagers but it seemed like a place that would be crowded to me so we stayed away.
Second City – Comedy, improv theatre founded in Chicago that has launched 1000 Saturday Night Live careers including Dan Akroyd, John Belushi, Eugene Levy, Mike Myers, and Joan Rivers.
House of Blues – live music in a very cool venue.
Chicago Sports Museum – we did not visit here but adding to my list for next time.
Shopping in the Gold Coast

The deep dish pizza is not my favorite personally but you have to have it anyway. Giordano’s and Gino’s are very similar – if I had to pick I would say slight preference for Giordano’s. It was very crowded (no reservations) but they are very efficient in their waiting and ordering system.

This one is from Pizzano’s. I really loved it too.

Bobby’s Bike Hike – this was SO much fun to do as a family.

My friend told me we looked like we are on the Chicago trash pick up tour with these vests on. Safety First!

The bike tour is a great way to see the architecture up close.

The famous Chicago Bean is a stop on Bobby’s Bike Hike.

The bike tour also takes you along the waterfront of Lake Michigan – that is by far my favorite part.

On the roof of the St. Regis. Traveling with your kids is such a bonding experience. I love you too, sweet Johnny.

Gibson’s Bar & Steakhouse – normally I do not like big steakhouse restaurants like this but I loved Gibsons. The vibe is fun and the martinis are cold.

For the carnivores in your life, of which I have many.

On the beautiful walk from the Peninsula to the waterfront.

Underground tunnel from the street to the waterfront.

Thomas quickly grew accustomed to the Peninsula lifestyle.

Ralph Lauren RL Chicago – like all RL venues, you instantly feel differently (happier and perhaps, more stylish just by being there?) when you walk into this restaurant.

Trying an oyster for the first time! Not sure there will be a second time sadly.

The aforementioned pigs in a blanket were a huge hit.

My handsome, sweet, funny stepson with an incredible work ethic who is such an important role model for my twin boys along with his brothers.

When you only pack one sweater for the weekend…

Do not sleep on the priority boarding tickets.

You really cannot miss this delicious little spot.

This is the best thing you have ever tasted.

Willis Tower, formerly Sears Tower Skydeck – get the timed tickets to skip all the lines.

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