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.