Whether you live here and need some inspiration on where to eat and what to do, or you’re visiting and have no idea where to start, this guide is for you. I’ve rounded up my favorite restaurants (places Rob and I love and visit frequently), the best spots to grab coffee or a drink, some amazing places to stay, and the best way to get around the city once you’re here!
Chicago has so much to see and do. If you’re planning a trip, I recommend visiting in summer or fall! After a long winter, Chicago truly comes to life in the summer. In fact, summer is exactly why we put up with those long winters.
Chicago has two airports—Midway & O’Hare. You can get to the city on the L or by cab/uber from either. They’re pretty equidistant from downtown.
Once you’re here, one of the best ways to explore the city is on foot. Chicago’s downtown is very walkable and one of the best ways to see all the sights!
We have amazing public transit, so take advantage. The L (elevated train) can get you just about anywhere for super cheap! You can buy a train card at any station.
The L can get you most places, but not everywhere. Cabs & Uber/Lyft are prolific here—especially downtown, so when you need to go somewhere different or just get tired, that’s the best option!
TIP! Don’t rent a car and try to drive through the city. It’s easily accessible by public transit and cabs and will save you a whole lot of headaches.
Cloud Gate (The Bean): If you’ve never been to Chicago, you can’t really leave without seeing this one. It’s one of the most iconic things in Chicago, don’t forget to get a picture!
Grant Park: Just south of Millennium Park, this is where Buckingham Fountain is located and where Lollapalooza is held each year
Michigan Avenue: After you’ve seen Millennium Park, walk north up Michigan Ave. You’ll see the Wrigley Building, The Tribune Building, Water Tower Place, lots of shopping and eventually you’ll hit Hancock Tower.
Hancock Tower: The views from here are amazing! After your long walk, stop here and head to the top for a rest, a drink and stunning 360 views of the city and Lake Michigan.
River Architecture Tour: It’s best in the summer at dusk! We take all of our friends to do this when they visit. You get gorgeous views and some Chicago history wrapped up in one fun tour! There are multiple companies, but most of them leave from the intersection of the river and Michigan Ave. Just walk up and pick one!
Lincoln Park: When I first moved here, I lived close to Lincoln Park and walked through it nearly everyday with Oliver. It’s not only beautiful, but it also houses a few other sights like the Lincoln Park Zoo and the Conservatory, the latter being one of my favorite places to visit during winter.
Wrigleyfield: A must for Cubs fan or any baseball fan, Wrigleyville is full of bars too, so it’s a good spot and take a break in the afternoon or grab a quick lunch.
Navy Pier: This spot is a huge tourist attraction, but unless you have kids, I recommend skipping it. It’s full of tourist restaurants and isn’t really that authentic. Instead, take a walk through Olive Park and up the lakefront.
Skydeck at Willis Tower: Technically it’s called the Willis Tower, but locals still refer to it as Sears Tower. Here you can step out on the glass deck on the 103rd floor. I actually haven’t been here, and prefer taking guests to Hancock Tower, but it’d still be a cool thing to do!
Favorite Neighborhoods to Wander
Lincoln Park (get off at Fullerton and walk east), Gold Coast, Logan Square & Wicker Park (get off at Division and you’re right in the middle of six corners- tons of great bars, restaurants (Big Star is just there)