Best of Chicago: Top Attractions, Food, and More
Can I be honest with you here? I had never thought of Chicago as a place I wanted to take a vacation to. But then, I had the pleasure of being placed here for work for a few weeks and quickly fell in love with the city. Chicago is a beautiful city, especially if you love architecture. It’s also one of the cleanest and most walkable cities I have ever had the pleasure of being stuck in without a car. And I set out on a mission to discover the best of Chicago—the top restaurants, things to do, and destinations around the Windy City.
I have enjoyed walking through the neighborhoods of Streeterville, River North and East, and Lincoln Park. This city has an indefinite attention to detail, from the food to the attractions, and there’s a plethora of activities with something for everyone. One of my favorite things about Chicago is that so many of the restaurants source their ingredients from local farms and change the menu with the season. There are also many LEED-certified buildings in downtown, as well as recycling at every garbage can on the street.
Let’s highlight the best of Chicago below and get you some ideas for your itinerary!
While we explore the must-eats, nightlife, and adventurous activities in Chicago, I may include affiliate links in the post. If you decide to make a purchase through one, I could earn a small commission from the sale at no cost to you. Thank you so much for helping support my blog and mission!
Best of Chicago Restaurants: Farm-to-Table Goodness
Girl & The Goat
Located at 809 W Randolph Street, this foodie hotspot is a must if you can get a table. I had the pleasure of going here with my sister and nephew. We started off with a loaf of fresh bread with goat cheese baked in—delicious and there are a few options. Most of the dishes are made to share, so we ordered a bunch.
Highlights were the fried duck tongue on Ahi poke with black beans, duck fat french fries, fried squash blossoms, and the grilled octopus (which I could probably eat every day). It is a cozy environment, so if you like having lots of space and not talking to your neighbors, this may not be for you. It’s not a great place for kids, as there are few options other than bread and french fries that most kids would eat.
Avec
At 615 W Randolph St., I was dying to try a French restaurant when this spot was suggested by some friends in Chi-town. Avec was an intimate dinner place, having what seemed like space for about 40 people and communal tables, which always stirs good conversation (along with suggestions from your neighbors on what to order and what to not). Food highlights were the bacon wrapped dates, and chicken with goat cheese—because everything with goat cheese is delicious.
Sunda
This is a noteworthy Asian restaurant located at 110 W Illinois St. I’ve heard great things about it, but I was not able to try this spot yet. After a 30-minute wait on a reserved table and so much noise I couldn’t think, I was forced to go seek quiet shelter at a more intimate place for a bite to eat. Great for socializing but not for a quiet Friday night dinner.
ING
Located at 951 W. Fulton Market, ING is a gastronomy experience that you won’t soon forget. When I think of gastronomy, I think of foams and gels with weird flavors. I was pleasantly surprised at ING. Having a sampling of street foods, there wasn’t a course that I didn’t love and there were 10. With a menu that changes every 6 to 8 weeks, you will always be trying something new.
Bavettes
Les Nomades
Topolobampo: A Rick Bayless Restaurant
Located at 445 N Clark St., this is the sister restaurant of Frontera Grill and known for being a more gastronomical and elegant version of its sister restaurant with a rotating menu selected from different regions of Mexico. Being only 70 seats, this restaurant is known to be difficult to get a table in. I secured a table on OpenTable and went on a Thursday at 9:30 PM, which is the last seating. Staff insisted on ordering from the 5-course tasting menu.
I started with an appetizer of a trio of ceviches, which was the best part of the evening, save for the margaritas and dessert. The first course was an avocado and mussel salad, which tasted like clams and was not my favorite. There was also a beet and queso Fresco salad, which we spooned into tortillas and enjoyed. The second and third courses were fish. The sablefish was a fail but the halibut was good, and the steak with mole was delicious. Dessert was also great, but at $450 this does not get my vote.
Restaurant to Avoid: Grace
Stepping inside Grace at first glance reminded me of a mixture of a Japanese tea room and a wedding reception hall with a blah decor of white, grey and Beige. There were no windows and the tables are big rounds that make you feel very distant from your dinner partners. You are served by a team of what looks like CIA operatives who nervously place spoonfuls of gel and pudding on your table.
You can choose from two menus; Flora or Fauna. We did one of each, but save yourself the trouble and order the Fauna. The vegetarian menu was more disappointing than delicious. It’s a good thing they get everyone drunk here with the wine pairings because the food was a giant miss for me.
Best of Chicago Bars, Lounges, and Nightlife
- Gilt Bar: Quintessential wine and cocktail lounge come for drinks or dinner with a date
Violet Hour: Speakeasy feel in this Mixology bar with high chairs worthy of the Mad Hatter; great cocktail menu with no Cosmopolitans or Bud Lights, so be adventuresome and order one of their house specialties like the Juliet & Romeo - Three Dots and A Dash: Hidden & Intimate Tiki Lounge where your drinks might just bite back
- Honorable mentions: The Atrium and the super secret The Office
Best Rooftop Bars in Chicago
- J Parker: Great views of the lake, small plates and cocktails
- The Wit: Elegant, hip atmosphere with a moon roof that opens to the night sky; come for drinks, appetizers and late night
- Honorable mention: Terrace at the Trump
Best of Chicago Adventure and Health Activities
- Try a run through Millennium Park at night; don’t forget to stop at the fountains and take in the light show
- Rent a Bike & bike down the Beach or one of the many great museums
- Rent paddleboards at North Beach: Chicago SUP
- Give your belly a workout and visit IO or Second City for a night of improv and ridiculousness
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