Congratulations to the city of Chicago for being voted "The Best Big U.S. City" for the 5th year in a row by Condé Nast Traveler! As a celebration, we took a trip to this beautiful city, and from the skylines to the restaurants to the boutiques, we see why it keeps winning. Big shoutout to Choose Chicago for welcoming us in and guiding our trip. Whether you're traveling with friends, your significant other, or solo, Chicago is for everyone. Here's the ultimate Chicago travel guide.
where to stay
Thompson Chicago Hotel
Perfect for satisfying your luxury desires. Sitting in the Gold Coast neighborhood, this trendy, sleek hotel shows off Chicago's skyline right from your room, and it's in the heart of downtown surrounded by boutiques and restaurants. Fine dining downstairs at Nico Osteria, the peach cobbler french toast and truffle brussels sprouts are the ones to get. Friendly, helpful staff and luscious, comfy beds, we'll be back.
what to do
360 Chicago & TILT
94 floors up with breathtaking views in every direction, Lake Michigan and the whole skyline included. Ride the TILT if you're up for a thrill, a tilting glass lookout with views straight down from 1,000 feet. Nerve-wracking but worth it. Grab a drink at Bar 94 after, the strawberry gelato and the Captain America drink both stole the show. Plenty of seating, and extremely photo-worthy.
Immersive Van Gogh Exhibit Chicago
Brings his artwork to life in a way that's hard to describe, like walking through the paintings themselves, each stroke telling its own story. Big enough to walk around, but we'd suggest grabbing a seat and just taking it in. Gift shop after with everything from Van Gogh scarves to keychains, plus an on-site bar for chatting it up with friends once the show's over.
Lake & River Architecture Tour with Wendella
If you're near Riverwalk, this is a must. Seeing Chicago from the river completely changes the sightseeing game. Our 90-minute tour was relaxing and genuinely educational, we learned the history behind the city and its buildings, went through the Chicago Lock, and got a full view along Lake Michigan.
Flight Club
Interactive digital darts taken to another level, plus food that's actually good. Perfect for a night out and you don't need to be any good at darts to have fun, it's even better with a group. They've also got a location coming to Atlanta.
Chicago Bulls Game at United Center
Non-negotiable if you're a sports fan. We caught a win against the Cavaliers and the energy in that arena was through the roof. Don't miss the 17 ft. bronze Michael Jordan sculpture, "The Spirit," in the community area, and shoutout to Benny the Bull for the surprise silly string.
SkyDeck Chicago
The highest observation deck in the country, with views stretching into four states. The glass ledge box that extends out from the building is not for the faint of heart, you're standing directly above the city. Immersive exhibit on the lower level too. Ultimate spot for the skyline photo.
Lincoln Park Zoo
Free entry and genuinely fun no matter who you bring, family, friends, or a date. It's the fourth oldest zoo in North America and sits right in the heart of the city. We saw polar bears, giraffes, and a baby gorilla who had toddler energy the whole time we were there. Missed Mr. Rhino this time around, next trip.
where to eat
Summer House Santa Monica
More than the sunny aesthetic, the new American food and tropical drinks are the real draw. Felt like we'd been teleported to the Santa Monica coast in the middle of windy Chicago. Truffle fries topped in grated mozzarella to start, glazed salmon with mashed potatoes as the main, and the warm sea salt chocolate chip cookie with ice cream for dessert, all musts.
Nico Osteria
Downstairs from Thompson Chicago, in the Gold Coast neighborhood. Chic Italian, great for breakfast or a date night dinner. Peach cobbler french toast was the highlight of both our mornings, and the brussels sprouts appetizer might've been the best dish on the table. Servers were helpful, the atmosphere was great, this place is a genuine gem.
Beat Kitchen on Riverwalk
Best view of any restaurant we went to, dining right on the Chicago River. The bacon mac and cheese and their popular tacos, shrimp tacos especially, did not disappoint. Refreshing slushees on the drink menu too. Pair it with a riverboat tour after for the full afternoon.
Skyline, food, energy, Chicago backs up the hype in every direction. Five years running, and we get why.