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Plan Your Trip to Chicago: Best of Chicago Tourism

What is Travellers’ Choice Best of the Best?
This award is our highest recognition and is presented annually to those businesses that are the Best of the Best on Tripadvisor, those that earn excellent reviews from travellers and are ranked in the top 1% of properties worldwide.
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Chicago’s got the big-city vibes you want, but friendly locals and a walkable layout make it homey and accessible all at the same time. With 77 neighbourhoods to explore, your best bet is starting with the Loop or Gold Coast to hit the highlights, then fan out. Wander among the architecture that made the city famous or eat your way through town. You’ll hear a lot about deep-dish, but the tacos are also next-level, thanks to Chicago’s thriving Mexican community. If you’re there in spring/summer, spend a do-nothing day lounging lakeside or grab a patch of grass at one of its many parks. At night, both the music and comedy scenes have put Chicago on the map. (You can't go wrong, but Lincoln Hall and Second City are always a good time.) There’s lots more to dig into. We’ve got options below.

Travel Advice

Essential Chicago

A high-low eating tour of Chitown

Chicago is one of the great American restaurant towns, smashing at every level from gravy-drenched sandwiches to molecular theatrics. The city has mastered the high-low food experience like no other and it's what keeps me coming back again and again (I'm a food writer, after all). So if you're like me and love both, here's my list of recs. Bring your appetite.
Adam Erace, Philadelphia, PA
  • Cellar Door Provisions
    High: Cellar Door is clicking again post-pandemic with dinner-only hours and a no-bookings policy. While I miss their exquisite morning pastries (it used to open for breakfast, too), it’s good to be back in this stripped down Logan Square spot. My go to's: the Med-inspired treasures like flat-iron marsala, a white-out of burrata and blanc asparagus, and brown butter-rosemary gelato for dessert. A tip: Get there before they open at five, it gets crowded.
  • Pequods Pizza
    Low: There are plenty of options in town for deep-dish diehards, and this Lincoln Park outpost of Pequod’s is mine. Order a beer or two as you wait (a while) for the ferociously hot pan pizza to land on your table—its ring of caramelized cheese around the rim is gold.
  • Sun Wah BBQ
    High: The Cheng family is Chicago royalty, and Sun Wah is their kingdom. This sprawling institution is iconic and the menu is massive, but the thing to order is not on it: the Beijing duck dinner, a grand multi-course feast (go with a group) starring a roasted duck whose skin is as bronzed and crackled as the top of a crème brûlée. While you can order it once you arrive table, I recommend putting in the request when making a booking.
  • Dove's Luncheonette
    Low: This is the Tex-Mex fantasy diner of my dreams. Crispy hash, brisket tacos on house-made flour tortillas, chicken-fried-chicken, and horchata pie coexist with communal tables, penny-tiled floors, and friendly service. love Dove’s for lunch/brunch, but it’s also a terrific late-night pop-in for al pastor fries and a $5 mezcal shot.
  • Virtue Restaurant & Bar
    High: There are a hundred details that make Chef Erick Williams’s Hyde Park restaurant a pillar of Southern cooking in Chicago. Among them: the smoked turkey perfuming the collards, the turnip chow-chow on the salmon, the Carolina grits with the shrimp and crawfish etouffee. If you can’t get a booking, hang at the bar, which has a stacked wine list, as well as a handful of inventive non-alcoholic cocktails.
  • Johnnie's Beef
    Low: You didn’t think you were getting out of this list without an Italian beef recommendation, did you? Everyone in Chicago has a favourite held close to their heart, but it’s hard to do better than Johnnie’s. Their beef is shaved so thin you can almost see through it, and their giardiniera pops like the Bangsnaps you used to throw at the sidewalk as a kid.It's cash only and a little out of the way in Elmwood Park but so worth it. I like to go on my way to/from O’Hare airport.
  • Mi Tocaya Antojeria
    High: “Nuestro cocina, nuestro amor” (our cooking, our love) is the motto at Mi Tocaya. If you ask me, Diana Dávila is maybe the most talented Mexican chef in a city jam packed with terrific Mexican restaurants. Her colourful, casual dining room in Logan Square is the ideal spot for dishes like braised pork shank in a secret mole sauce and chiles en nogada (made here with Brussels sprouts). Bonus: the drink list is as comfortable around natural wine as it is margaritas.