Although it has been a little while since we went to Chicago for our annual mother-daughter trip, I get asked for this itinerary quite often! We LOVED Chicago! It was such a fun and unique city with lots to do and lots to see. We spent 4 days exploring, shopping, and eating the most delicious food!
Day 1: Mag Mile & Architecture Tour
As per most of our mother daughter trips, when we arrived in the Windy City, we laced up our tennies and hit the ground walking! We checked-in to our hotel, the Millennium Knickerbocker Chicago, before stepping out onto the Magnificent Mile. The hotel was nice, clean, and in a fabulous location for exploring the city by foot!
The shopping along the Mag Mile is ah-mazing! From high end stores to trendy boutiques, it has it all! After making a few purchases to kick off our trip, we worked up an appetite. Chicago’s deep dish pizza is something everyone has to try, am I right? There are several places in Chicago that are known for their fabulous pizza, but our research led us to the top two – Giordano’s or Lou Malnati’s. Apparently if you are a local or frequent visitor in Chicago, you are probably partial to one or the other, but I really don’t think you can go wrong. For convenience purposes, we enjoyed a not-so-light lunch at Giordano’s Pizzeria, and it was oh so yummy!
After lunch we headed to the river to enjoy an architecture boat tour. While I’m not typically one to spring at a guided tour, especially for architecture, this was highly recommended and ended up being one of the trip highlights! We chose to go with Wendella Boat Tours, and purchased our tickets several weeks in advance. Be sure to get to the boat ramp early for a good spot in line and ensure you get great seats! Another highlight for Wendella’s Tour – there’s a bar! 🙂 We had the most perfect weather for the boat tour – but Chicago weather can certainly be a bit extreme, so that’s something to keep in mind when booking your tour!
It just so happened that my sweet sister in law was also on a girl’s trip in Chicago while we were there, so we decided to meet up for drinks! We met for cocktails with a view at The Signature Room right at sunset. The cocktails were good, but oh my goodness the views were amazing! Tip – be sure to go to the ladies bathroom, it has some of the best views of all! We later enjoyed a late dinner at Girl & the Goat, which was also highly recommended by many! It is a tapas-style restaurant and was so delicious! The same restaurant also owns Little Goat Diner, which I’ve heard great things about as well!
Day 2: Biking & The Bean
After grabbing our morning coffee, we headed out for an adventurous day. This crew LOVES a good bike ride – maybe even more than walking, which is saying a lot. However, biking in a big city can be a little bit daunting. Thankfully, Chicago has a beautiful waterfront biking and walking path that makes it quite an enjoyable mode of transportation. We picked up our bikes at the Divvy stand near our hotel, but they can be found all over Chicago. You download the Divvy App on your phone to locate the bike stands and use a credit card to pay. You can take the bike for a quick 30 minute ride for $3, or purchase a day pass for $15, which includes unlimited 3 hour rides in a 24 hour time period.
We didn’t really have a set plan for our bike ride, other than to end up at The Bean. We were able to explore Navy Pier, Grant Park with Buckingham Fountain, and the Museum Campus. We are the type of group that prefer being outdoors versus exploring museums TBH, but Chicago is known for their outstanding museums! The Field Museum is a fabulous choice if you just pick one.
Our biking adventure concluded at Millennium Park, home to the famous Cloud Gate, aka The Bean. It’s one of the must-see landmarks in Chicago, of course! It sits in a gorgeous park with playgrounds and lots of green space. The tulips in the park, and throughout the whole city were so beautiful. Go, snap a photo, and then you can say Bean There, Done That!
Just across the street is the Chicago Athletic Club, where you will find Cindy’s Rooftop. This was definitely our favorite meal of the trip, and that’s saying a lot. The food and drinks were incredible, and the views were even better. It’s also just a really fun atmosphere, especially on a pretty day.
We spent the remainder of the day doing a little bit more shopping and exploring on foot, before heading back to the hotel to get ready for the evening. We made reservations for RPM Italian, which is a delicious Italian restaurant owned by Giuliana & Bill Rancic. After dinner, we found ourselves on stage at the Howl at the Moon Piano Bar! We let our mothers retire to bed, and the young gals headed over to Three Dots and a Dash, a cute speakeasy tiki bar.
Day 3: SkyDeck, Riverwalk, & Second City
Chicago is home to the famous Willis Tower, which is formerly Sears Tour. For a good 25 year run, it was the tallest building in the United States, only recently surpassed by the One World Tower in NYC. We started our morning off with some exceptionally “high” standards, and let’s just say we didn’t need that coffee to wake us up! We made early reservations at the SkyDeck Tower, where you can stand on The Ledge. The Ledge is a clear glass box that sticks out about 4.5 feet from the side of the building, more than 1,300 feet above ground!
The rest of the day was spent exploring on foot. We walked back toward the Mag Mile through the Theater District and along the Riverwalk, browsing along the way. We enjoyed a delightful bite at Eataly, and finished it off with Limoncello. They even have a Nutella bar there!
We headed back to the hotel early to get ready for our 4:00pm show at The Second City. YALL. We are literally still laughing about that show! The Second City is a well-known comedy club where several famous comedians got their starts – Bill Murray, Tina Fey, Amy Poehler, and Steve Carrell to name a few! It can certainly be a bit crude at times with adult humor, but it is hilarious.
After the show, we grabbed some rooftop drinks nearby at the swanky J Parker before heading to another delicious meal at Gibsons Steakhouse. If you are a steakhouse lover, you can’t miss this one! The mother headed home after dinner, and the young ladies had a fabulous time at Kingston Mines, a blues music bar to cap off a fabulous evening.
Day 4: Wrigley Field & High Tea
So although baseball fields and afternoon tea don’t typically go together, we wanted to be sure to fit in all of our extra-curriculars, and that’s just the way it worked out! But first, we started our morning with a quick walk along the LakeShore Trail and then heading to a divine brunch at Fig & Olive. Ok, so maybe that was my favorite meal of the trip? The meals were just ALL so good!
After brunch, we ubered to Wrigley Field to walk around. There was an away game later that day, so “Wrigleyville” was buzzing with lots of fans watching the game from hole-in-the-wall dives. We always enjoy checking out the baseball stadiums whenever we travel to a new city, and Wrigley definitely didn’t disappoint!
We closed out our trip in the very best way, pretending we were royals and having high tea at Palm Court in the Drake Hotel. I have never had a true high tea experience, and it was so much fun! The staff was so kind and informative, as well as very helpful in showing us exactly how it should be done. We were served tea along with a beautiful tiered tray of sandwiches and pastries while a harpist played in the background. Ah-mazing. You’ll definitely need a reservation for this pretty well in advance. The Drake was literally across the street from our hotel, making it easy to grab our bags and catch our flights back home!
We had a wonderfully packed 4 days, and while we covered a lot of ground, we have plenty more reasons to return! Some additional things to do and restaurants that were also recommended to us by friends…
THINGS TO DO: Navy Pier Amusement Center, Shedd Aquarium, Lincoln Park Zoo, The Tilt and 360 Chicago Observation Deck (John Hancock Tower)
RESTAURANTS: Au Cheval, Purple Pig, The Aviary, Doughnut Vault, Publican, Seven Lions, Cafe Babareeba, Fulton Market Kitchen
DRINKS: Drum Bar, Zebra Lounge (piano bar), California Clipper (jazz bar), Broken Shaker
We had the very best time in Chicago, and we can’t wait to return again!