Chicago: My First Visit — Where I Stayed and the Best Places I Ate

At the end of October I took my first trip to Chicago and had an incredible time. The city’s architecture, lakefront views, and neighborhoods made exploring easy and enjoyable. I also ate my way through several excellent restaurants, so here’s a concise recap of where I stayed, the places I loved, and a list of highly recommended spots I didn’t make it to but want to try on my next visit. If you’re planning a trip to Chicago, this guide will help you prioritize great food and a comfortable base.

We stayed at The Thompson Hotel in the Gold Coast, and it was a perfect choice. The hotel is stylish and cozy, with attentive service and a great location—just steps from the lake and within walking distance of the stores along The Magnificent Mile. Chicago is a large, spread-out city, but from the Thompson it was simple to reach many neighborhoods. We enjoyed breakfasts in bed, comfortable rooms, and evening appetizers and cocktails at the hotel restaurant, Nico. Highly recommended as a base for a first-time visit.

Now for the best part: the food. Below are the places I ate and absolutely loved.

• Au Cheval — A modern, diner-style burger destination that genuinely lives up to the reputation. We arrived early to avoid the famously long line and were rewarded with one of the best burgers I’ve ever had. My husband ordered the fried bologna sandwich, which was melt-in-your-mouth delicious. This is a must-visit for burger lovers.

• AVEC — A cozy spot serving modern Mediterranean-inspired small plates. We enjoyed a late dinner after an event; highlights included chorizo-stuffed, bacon-wrapped dates and other shareable dishes with bold flavors.
• Le Colonial — Just around the corner from our hotel, this Vietnamese restaurant was our arrival-day stop for a late lunch. The food was flavorful and classic—an excellent introduction to the city’s dining scene.
• Girl & The Goat — Chef Stephanie Izard’s famed restaurant was worth the hype. We celebrated a birthday with a variety of small, globally inspired plates and enjoyed every dish. It’s lively, inventive, and perfect for sharing.
• The Aviary — For a special cocktail experience, The Aviary is unmatched. The drinks are theatrical, inventive, and potent—plan accordingly. The service and presentations make it a memorable stop before dinner or as a night out on their own.
• Cindy’s Rooftop — This rooftop bar offers stunning views of the lake and Millennium Park. It’s very close to the Cloud Gate (“the Bean”), so it’s easy to combine sightseeing with a memorable drink or light meal.

Below are additional restaurants and bars recommended by Chicago locals and foodie friends—these are on my list for next time:

• Kai Zan Sushi — Known for exceptional omakase service.
• Duck Duck Goat — Another Stephanie Izard concept focused on bold Chinese-inspired flavors.
• La Scarola — A classic, old-school Italian spot beloved by locals.
• RPM Italian — A popular choice for celebratory Italian dinners.
• Purple Pig — Known for its shareable Mediterranean dishes and lively atmosphere.
• Eataly — A large Italian marketplace with multiple dining options.
• Pequod’s Pizza — Frequently recommended for classic Chicago deep-dish pizza.
• Portillo’s — A local favorite for Chicago-style hot dogs and Italian beef sandwiches; try the Italian beef with hot giardiniera and fries.
• Lone Wolf — West Loop bar with a notable whiskey selection.
• Maude’s Liquor Bar — A popular West Loop spot for drinks and comfort-forward dishes.
• R&M Champagne Bar — Another West Loop destination for cocktails and champagne.
• Do-Rite Donuts — For fantastic donuts and coffee.
• Greek Islands — Classic Greek cuisine in Greek Town.
• Big Star — Known for great tacos and drinks in Wicker Park.
• Monteverde — A modern Italian spot often praised for inventive pasta.
• Hai Sous — Southeast Asian-inspired small plates and flavors.
• Fat Rice — Praised for unique Macanese-influenced dishes.
• Mott Street — Noted for its Southeast Asian flavors and creative menu.

That covers the highlights from my first Chicago trip. I’m already planning a return to explore more neighborhoods and try the other spots on this list. Chicago felt warm and welcoming, and the food scene was varied and exciting. If you’re from Chicago or have favorite places I didn’t mention, please share your recommendations—I’ll add them to my list for next time!