In late 2019, I headed to Chicago (for the first time) with family to support my older brother who was running the Chicago Marathon. Coincidentally, I needed to be there for a work conference a few days after the race, so the stars aligned. We had several days spent eating, drinking and exploring our way through the incredible windy city. Here are my ultimate 19 things to see, do and eat!
1. Catch a Bird’s Eye View
Catching a bird’s eye view whilst in the city is a must! We went up 1353 feet to the Sky Deck in The Willis Tower. It was extremely busy, so we bought the fast pass to save us a couple of hours in lines. Make sure to line up for “The Ledge”, a glass box that juts out 4 feet from the 103rd floor, giving the appearance in photos that you’re floating in midair! Your time in the ledge might be limited and regulated like ours, so move quickly to get the photos you want!
2. Visit Cloud Gate in Millennium Park
Chicago’s “bean” in Millennium Park is perhaps the most iconic symbol of Chicago (next to the deep-dish pizza, of course). Don’t visit the day before the marathon like I did if you wish to get up close and personal with the bean! I revisited a second time early the morning after the marathon for a much better experience and photo op!
3. Do a Cheese Pull
The deliciousness of Chicago’s Deep-Dish Pizza needs very little introduction! I couldn’t believe it was my first time ever trying it. It was so nice I had to do it twice! Giordano’s was my restaurant chain of choice after some very important pizza research! Best eaten whilst piping hot so you can achieve a mandatory “cheese pull”. Beware of the 45-minute cook time required to cook a perfect pie – you may want to order ahead or warm up at the bar while waiting!
4. Chicago Theatre
The Chicago Theatre in the Loop Area is listed as a city landmark and is an “unofficial emblem of the city”. Nothing personal against Peppa Pig, but we didn’t attend a show here, so had to appreciate the beauty of the building from the outside.
5. Riverboat Architecture Tour
Whilst a tad bit chilly, this was such an informative way to learn about the history of city including the Great Chicago Fire in 1871, and the “great rebuilding” in the decades since which was has had several distinct periods of architectural styles. It was also a great vantage point to appreciate the grandeur of the skyscrapers, and the beautiful city in general.
6. Rosé All Day
What’s a holiday without long lunches a la Rosé. Our place of choice was the Hampton Social River North. Everything was tasty, the Rosé crisp and dry, and the atmosphere relaxed to accommodate our extended stay!
7. Indulge at Bombobar
Located in Chicago’s West Loop, this place merges donuts and ice cream to create a little piece of heaven. Choose your gelato flavor and top with donuts infused with whatever filling your heart desires or opt for an ice cream sandwiched within a donut and topped with all the goodies! I opted for the waffle cone filled with charcoal oreo gelato, and a Nutella infused donut on top.
8. Walk Everywhere
Chicago was such a walkable city for the most part, and I visited in fall which made for crisp air and trees boasting all the beautiful autumn tones. While the subway system was very efficient for longer distances, life above the ground was so much more enjoyable. Walk wherever you can, and preferably along the Riverwalk! We certainly needed to with all the eating and drinking on our agenda!
9. Chow down on Garrett’s Popcorn
Garrett’s Popcorn has many locations dotted around the city, providing convenient access to the best popcorn I have ever tasted!! I got the cheese, and the salted caramel, and I’m torn on making a decision between which was best. It’s such a great gift to bring home. After all – edible souvenirs are the absolute best.
10. Brunch in the city
We brunched at Dusek’s Board & Beer in the Pilsen neighbourhood. It’s a no-frills gastropub serving soul food in a dark, cozy atmosphere which is warmed by a wood-burning oven. The Ricotta beignets were to die for! Other highlights included the Chilaquiles, banana bread, and hot chicken & waffle! We understood why it has been awarded one-star in the Chicago Michelin Guide for several years.
11. Spectate the Chicago Marathon
The energy in the city during the week of the marathon was out of this world. Thousands of people flocked to the city to challenge their physical and mental limits, for personal and/or charitable causes. Thousands more, including ourselves flocked to support those running it, with music, words of encouragement, ringing bells and signs to show our love. It was truly inspirational to see people of every type, age and background doing something so remarkably challenging.
12. Drinks on a Roof Top Bar (Cindy’s Rooftop)
It was incredible to see how well my brother held up after completing the marathon! He still had energy to head to Cindy’s Rooftop for champagne and snazzy cocktails to celebrate. Located at the top of the beautiful Chicago Athletic Association Hotel, the views of the millennium park down below are most certainly worth taking a trip there for, so is the vibe, and tasty nibbles.
13. Eat at a Michelin Star Restaurant (or two)
To celebrate my brother finishing his first ever marathon, he booked a table for 6 MANY months in advance in the kitchen (yes, in THE KITCHEN) at the world renowned, 3 Michelin starred Alinea restaurant. Alinea frequently makes an appearance on the world’s top 50 restaurants, and is widely known for Grant Achatz appearance in a Chef’s Table episode. The gastronomic experience uses music, lighting, colours, textures, and wines to compliment each course. The meal builds up to a dramatic end where everyone is served with an edible candied helium balloon whilst two chefs use dessert components to ultimately create a live masterpiece to the beat of the music, which is nearly too beautiful to eat! I’ll likely never eat a meal as pricey in my life, but I’ll always remember this as the ultimate gastronomic experience.
14. Drinks at The Aviary
Following dinner at Alinea, the staff got us reservations at Chef Grant Achatz’ nearby cocktail bar, The Aviary. It serves creative and innovative cocktails that give you more than a drink, but an experience. It is an extremely fine dining approach to cocktails, using rare ingredients, infusion flasks, evaporators, blast chillers. It was a bit like a science lab! :)
15. Stroll the Navy Pier
We took the architecture boat tour from the Navy Pier location. It’s the perfect place for a leisurely stroll along the water, or to grab a drink, hop on the Ferris Wheel, or watch a sunset with a skyline view.
16. Take a Self-Guided Graffiti tour
Chicago is home to a large creative community, which comes hand-in-hand with cool graffiti art (even though it’s not welcomed by the Chicago Department of Streets and Sanitation). While I didn’t have the time to extensively explore all locations I’d hoped to, it was still great to appreciate the splashes of colour and art throughout the city. Two pieces I would have loved to see art the flamingo graffiti at the Flamingo Rum Club, and the Greetings from Chicago graffiti on Milwaukee avenue. Next time for sure!
17. Eat at a Rick Bayless Restaurant
The esteemed Rick Bayless has dedicated most of his career to creating world renowned Mexican cuisine, so we had to check out the hype. We dined at the one-star Michelin restaurant on our first night. It was my first time having a refined, elegant, high-end Mexican meal. It’s hard for me not to associate Mexican with a hearty burrito or saucy enchilada, but I must admit the quality of the ingredients in all 6 courses were carefully selected and paired, the flavors were vibrant, and the experience fantastic! That being said, Rick’s unassuming restaurant Torta Frontera serving no-frills, and delicious food in the airport made me
just as happy as the fancier sister restaurant! It’s rare to get great airport food after all.
18. Stay somewhere central
We stayed in a gorgeous Air BnB in the Loop Area extremely close to millennium park, the Chicago Theater, and lots of shops, which was a convenient base for our abundant exploring.
19. Stephanie Izzard any and everything
Save the best for last they say, and so my last mention of restaurants were my foodie highlights in Chicago. Stephanie Izzard’s restaurants blew me away. I say “restaurants” because I visited three of them. Cabra, perched on top of the Hoxton Hotel serves Peruvian cuisine, and is the newest addition to her restaurant collection (and also my favourite). Girl and the Goat is Stephanie’s first restaurant in the West Loop and it lived up to its hype. I loved shareable small dishes, as it gave us the opportunity to fully explore both menus. I also got the opportunity to dine at Little Goat for lunch, Stephanie’s no frills diner which serves simple but delicious meals.
That wraps up the top 19 list. Please do drop a line if you agree with any of my top 19, or if you perhaps have others you’d add if it was your list - I will be heading back to Chicago at some point after all!
