Chicago will always be a special place for me. Growing up in the suburbs and living in the city for a few years as an adult near Wrigley Field, it’s always going to be home for me. Whether you are visiting for a day, a long weekend or a full week, here’s a few of my favorite thing about Chicago and places to consider on your visit when you explore this underrated destination.
Bakeries & Sweets
If you have a sweet tooth, don’t skip these:
- Sweet Mandy B’s – classic, no-frills bakery vibes. My favorite is the iced sugar cookie, but there are so many delicious options
- Levain – Go for the thick, soft cookies.
- Jeni’s Ice Cream – not a bakery, but it earns its spot on this list. Consistently some of the best ice cream you’ll have.
- Molly’s Cupcakes – fun, playful cupcake spot that’s worth the stop.
- Summer House Santa Monica – technically a full restaurant (great for brunch too), but their cookies alone are worth a special trip.
Dinner
Chicago’s dinner scene is stacked, and West Loop is doing a lot of the heavy lifting. It has a great food scene and places to grab drinks before or after your meal. Here’s where to check out on your visit:
| Restaurant | Cuisine | Neighborhood |
|---|---|---|
| La Josie | Mexican | West Loop |
| Au Cheval | Burgers | West Loop |
| Lou Malnati’s | Deep dish pizza (chain) | Multiple locations |
| Siena Tavern | Italian | River North |
| Cafe Ba-Ba-Reeba | Spanish tapas | Lincoln Park |
| Bavette’s | Steak | River North |
| Green Street Meats | BBQ / drinks | West Loop |
| Lena Brava | Upscale Mexican | West Loop |
| Sunda | Asian | River North |
| Girl & the Goat | New American | West Loop |
| Monteverde | Italian with a twist | West Loop |
| Twin Anchors | Ribs (casual, been around forever) | Lincoln Park |
A few honest notes: Au Cheval and Girl & the Goat are Chicago institutions for a reason, which also means they’re famous for long waits. Go at off peak times or plan for drinks somewhere nearby for Au Cheval as it does not take bookings. Green Street Meats is a great one if you want food and drinks in the same stop and happy to just walk-in for a good, casual vibe
Brunch
- Summer House Santa Monica – bright, beachy vibe and a menu that’s hard to go wrong with.
- Beatrix – reliably good, easy to bring a group.
- 3 Arts Club Cafe – gorgeous setting (it’s inside a historic building with a courtyard) and a lovely option to try once.
Rooftop Bars
Best for golden hour with a skyline view:
- Cindy’s – the view over Millennium Park and Grant Park is unbeatable. A top pick for new visitors to Chicago
- J. Parker – found in Lincoln Park with great atmosphere on a summer evening.
- LondonHouse – classic Chicago rooftop with a killer river and skyline view.
Things to Do
- Millennium Park & the Bean – iconic spots in Chicago to see
- Grant Park and Buckingham Fountain – big park that’s nice to wander through and provides great views of the skyscrapers
- Architecture river cruise – genuinely one of the best ways to see the city and understand its skyline. Pick a nice weather day to take the river cruise. It’s a local and tourist favorite for a reason, a must-do.
- Riverwalk stroll – walk along the river and stop for a glass of wine or a quick bite along the way.
- Shopping on Michigan Avenue – the Magnificent Mile lives up to the name.
- Willis Tower Skydeck – go to the top for the views (and the glass ledge, if you don’t mind heights).
- Cubs game at Wrigley Field – grab a bite to eat nearby (maybe on Southport Avenue or Clark Street) and then definitely stop in some bars on Clark Street pre or post game to get the full experience. This is such a fun way to spend an afternoon
- Lincoln Park – full of great restaurants and shopping, especially along Armitage Street.
- Second City – Chicago’s legendary improv comedy club. A fun, easy night out.
- Lakeshore Path run (or walk) – start and end at Oak Street Beach for a scenic run along the water. Pick your distance, but this is always a favorite of mine.
- Navy Pier – classic tourist stop, with the famous Ferris wheel
- Kayaking on the Chicago River – a completely different way to see the city and its architecture.
- Local breweries – Goose Island and Lagunitas are the two big names, but there are tons of smaller spots worth stopping into for a tasting. Corridor Brewery, about a mile from Wrigley Field, has always been a favorite of mine
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