Memories from my Chicago bachelorette - Millennium Park - Anish Kapoor’s Cloud Gate (The Bean) sculpture
My ‘Unofficial’ Bachelorette in Chicago!
For as well travelled as I am, there are still so many places in the US that I have yet to visit. I am definitely guilty of returning to the same place several times, but I had never been to Chicago and there was something about it that I have always found alluring. Perhaps it’s its major metropolitan appeal, its beautiful architecture or its world renowned restaurants, but Chicago has always been a place I have wanted to go and, coincidentally, I am not the only one.
Rewind to this past winter, I was out at this cool French restaurant in Toronto with my two girlfriends, Emma Bain and Jocelyn Teng, and I had just asked them to be part of my wedding party. Instantly the topic of what we would do for my bachelorette came up and I could tell the girls were excited at the prospect of a trip. Of course the usual New York and Miami suggestions came up but none of it really excited me. ‘How about Chicago?’ I said. ‘I’ve never been!’ Excitement swept across the table. ‘Neither have I’, said Jocelyn, ‘Same!’, said Emma, and just like that it was decided!
I did have a special ask of the girls though. As much as I wanted to go to Chicago, bachelorette traditions like wearing a sash and being paraded around town is not my vibe. I would much rather go to nice restaurants, experience the city and do more than just drink. Of course cocktails would have their place in the itinerary but doing an Architectural boat tour of Chicago, eating at a Michelin star restaurant and checking out ‘The Bean’ were also a top priority among the group. And with that planning commenced for my ‘unofficial’ bachelorette weekend in Chicago.
If you want to see a day-by-day breakdown of our Chicago weekend itinerary, you can watch my travel vlog below. Otherwise see what rose to the top as our favourite activities below!
Things to do in Chicago
Aboard the CAC River Cruise’s Chicago's First Lady Architectural boat tour!
When it comes to standout experiences from our trip, the architectural boat tour definitely took 1st place. Truly the best way to see Chicago - 90 minutes on CAC River Cruise’s Chicago's First Lady flew by so quickly. Not only was the guide captivating with her storytelling, but the weather was incredible which made spending the afternoon on the water in the sunshine bliss. The girls and I not only learned so much about Chicago’s history and architecture, but we also relished in the opportunity to relax, take in the sites, and sip cocktails after an active morning exploring. The boat itself has an open air upper deck, a large front deck and a climate controlled interior salon with a full service cocktail and snack bar. We showed up 20 minutes prior to departure and it’s a good thing we did because the queue was already starting to build. Once passengers were let on board there was a bit of a rush to find a good seat and thankfully we secured three at the front of the boat. The cruise first moved west towards Goose Island before turning around and making its way south. Once at River City, the boat turns around again and heads back north east to the mouth of Chicago River where passengers get an opportunity to snap pictures with the entire Chicago skyline as a background before returning to the dock.
Hot tip: bring a light cover up or a hat if you are worried about getting too much sun as there aren’t really any shady areas to sit outside.
The girls and I at Millennium Park in Chicago visiting Cloud Gate (often referred to as ‘The Bean’)
Talk about cultivating joy! Our Saturday morning adventure to Chicago’s Millennium Park ended up being, hands down, one of the best parts of our trip! The girls and I were enamoured by Anish Kapoor’s Cloud Gate (aka The Bean Chicago) and spent at least a half hour walking around it, filming ourselves inside it, taking videos and snapping photos. It was surreal to see the sculpture in person and made our leisurely morning in Millennium Park before the Art Institute opened, one to remember.
Centrally located in the heart of Chicago’s downtown, Millennium Park is a lakefront campus where you will find interactive fountains, tranquil gardens, free events, public art, skating rinks (in the winter), rock climbing, and plenty of green space. It is also home to Frank Gehry’s Jay Pritzker Pavilion & The Great Lawn where a free summer series workout class was being conducted. Since the girls and I had some time to kill we continued our walk around Millennium Park to the Crown Fountains, an interactive video sculpture fountain by conceptual artist Jaume Plensa that features two towers with LED scenes that display enormous faces of Chicago locals. In the summer, the towers cascade with water and wouldn’t you know, Emma kicked off her shoes and went right in.
Since Emma is a galleriest and Jocelyn is an amazing painter, I knew we were going to enjoy our visit to the Museum of Contemporary Art, but what I didn’t realize was just how much we were going to love the featured exhibit! The main floor featured a couple of Canadian artists including Duane Linklater and Lotus Laurie Kang, which was a pleasant surprise, and the Gary Simmons Public Enemy exhibit was unbelievably powerful and moving.
Hot tip, their gift shop is incredible and way better then the Art Institute of Chicago. So if you are looking for little gifts or souvenirs to bring home, you’ll definitely find them there! The girls and I spent a leisurely hour and a half at the museum on our last morning in Chicago and although we preferred it over the Art Institute of Chicago (which was also great), our preference had to do with the current exhibits. That being said both museums are worth going to but which one is better will depend on what exhibit is on during your visit.
Jocelyn Teng checking out Edward Hopper's Nighthawks, part of the permanent collection at the Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and largest art museums in the world. It’s full of iconic works like Georges Seurat's A Sunday on La Grande Jatte, Edward Hopper's Nighthawks, and Grant Wood's American Gothic. The girls and I received Fast Pass admission to the Art Institute of Chicago with our Chicago CityPASS and spent a good chunk of Saturday morning wandering though its many galleries. Although lower on this list of things to do, we really did enjoy our time at the institute. Unfortunately we all had seen many pieces from the travelling Van Gogh exhibit currently on display, but there were many pieces in their permanent collection that were new to us. It is also a great way to work up an appetite for brunch.
Fun Fact: Ferris Buller’s Day Off’s iconic art museum scene was filmed at the Art Institute of Chicago!
Our visit to Chicago’s trendy Wicker Park neighbourhood was short but sweet. Our day had been full of activity already but as the sun began to set, we arrived at Wicker Park for a quick stroll down Milwaukee Ave. Wicker park’s Milwaukee Ave is full of trendy stores, music clubs, cafes, restaurants and cool fashion boutiques. The girls and I did pop into a few just to check them out quickly but given how lively our day was up to this point, we were more interested in sitting down and getting a drink. Needless to say, we found just that and more at the rooftop of The Robey Hotel located at the base of Milwaukee Ave. Here we took in skyline views of Chicago and a round of tropical cocktails during sunset. It was just the relaxing afternoon activity we desired and the perfect way to unwind before dinner. Had we had more time in Chicago I am sure we would have gone to brunch in Wicker Park and visited a few more of the vintage stores but alas, it will have to wait until next time.
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Chicago Restaurants
Highlights from our dinner at Sepia - Ricotta Cavatelli with Parmesan butter, pine nuts and crispy sourdough
Our Michelin Star restaurant experience at Sepia was well worth the splurge! Known for their inventive American cuisine, we dined at Sepia on our first night in town. We decided to each order a different dish and share so we could try almost everything on the menu. The food, the presentation, and the service were all spectacular and made for a beautiful evening.
Currently, Chicago is home to 23 Michelin Star restaurants so even if you can’t snag a table at Chicago’s famed three Michelin Starred restaurant, Alinea , there are so many outstanding dining experiences to be had. I may not be the kind of girl willing to wear a sash and be paraded around on her bachelorette, but I am the kind of girl who enjoys getting all dressed up and going out to a nice dinner to celebrate! Know what I’m saying!
Chef Thai’s famous crispy chicken wings from HaiSous Vietnamese Kitchen
HaiSous Vietnamese Kitchen, located in Chicago’s Pilsen neighbourhood was clearly made for foodies. The vibe is refined Vietnamese and considering they have been Nominated four times for a James Beard Award and have received 5 Michelin Bibb Gourmand, for the price it’s a steal. Service was impeccable but more importantly, the food was show-stopping. The girls and I accidentally ordered way to much but I am happy to say Chef Thai’s famous crispy chicken wings made it back to our hotel room and I will vouch, they made for a great snack the next morning!
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Chicago Brunch Spots
Duck Duck Goat in Fulton Market - a delicious dim sum brunch!
Our last meal of the trip was a delicious dim sum brunch at Fulton Market’s Duck Duck Goat! We started off with a round of cocktails before diving in to house made soup dumplings, spring rolls, their famous duck fried rice omelettes and a bowl of their delicious, hand-pulled, spicy noodles! The food was so delicious, inventive and energizing, and was one of our favourite meals of the trip! Duck Duck Goat is Chef Stephanie Izard’s third venture with Boka Restaurant Group and after our brunch experience at Duck Duck Goat I’m intrigued to try out their other restaurants ‘Girl & the Goat’, ‘Little Goat’, and ‘Cabra’ too!
The Pain Plissa;adoere from Obélix Chicago
After our morning at the Art institute of Chicago, the girls and I headed to Obélix in Chicago’s River North neighbourhood for an upscale French brunch. From escargot, to the foie gras Monte Cristo (their take on French toast), Obélix does a decadent brunch right. Although we did enjoy our meal at Obélix when it came to ranking our dining experience, this brunch came last. Perhaps we are spoiled with good French restaurants in Toronto or perhaps it was just that they had really steep competition. Either way it was good, just nothing to write home about.
The cafe inside Venteux, a french brasserie in downtown Chicago.
Our first morning in Chicago the girls and I stumbled upon Venteux while walking to Millennium Park. In desperate need of a good morning coffee, we crossed the street to check it out. A gorgeous French brasserie, cafe and oyster bar, the restaurant features a front cafe with outdoor patio seating and large dining room in the back. Since hunger had yet to strike, we grabbed a couple of ice coffees and a few pastries before continuing on our walk to Millennium Park. But there is no doubting this spot’s appeal and given their coffee was good I was left definitely wanting more.
Chicago Cocktail Bars
One of the cocktail presentations from our night at Aviary in Chicago
After our Michelin Star dinner at Sepia, we headed out for a nightcap to Alinea Group’s Aviary. We didn’t have a reservation and were a little worried about just showing up, but it seemed like luck was on our side because we managed to snag a table fairly quickly. The bar’s decor felt a little dated (it was giving airport lounge vibes) and the crowd was definitely more mature (not surprising considering cocktails start around $20), but we really enjoyed our evening of elaborate presentations and deliciously creative cocktails. It was a great way to end the night after such a fantastic dinner and a unique experience we all really enjoyed.
Determined to make the best of our last night in Chicago, the girls and I made our way to Three Dots and a Dash, A Polynesian tiki bar in Chicago’s bustling River North neighbourhood. The place was packed which made it challenging to get a drink but once we did, we had no problem getting in the dancing mood. The one thing I would do different is call ahead. Bar seating is very limited and there isn’t many great places to put your drink down. Had we had a reservation we could’ve sat down and ordered drinks from a waitress and gotten up to dance while still having a place to set our drinks down instead of standing the whole time.
All in all the girls and I had a great time on my ‘unofficial’ bachelorette trip to Chicago. There are so many fun things to see and do in Chicago, it’s hard to fit them all into one weekend. If you have any questions or comments about our trip to Chicago, feel free to leave them in the comments below. I’ll also be posting more wedding content soon so don’t forget to subscribe to my YouTube and Instagram pages! Until next time!
- Soheila
MORE BTS PHOTOS FROM THIS TRIP TO CHICAGO
