Local's Guide to Food, Hotels & More in Chicago, Illinois
Arts & Culture
Food & Wine
Chicago (my hometown) is the best city in the US - and I'm not biased or anything! Between the beautiful lakefront and amazing architecture, you will find museums, restaurants and shopping galore. I will be bold and say Chicago also has the best public transportation system I have experienced. For being one of the biggest cities in America, Chicago doesn’t feel overwhelming. One of the best sports towns and home to Second City, Chicago has it all.
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Where to stay in Chicago, Illinois
The Peninsula Chicago
Elegant luxury hotel located in a high-rise in downtown Chicago.
$100 hotel / resort credit.
Upgrade & extended check-in/out whenever possible.
Waldorf Astoria Chicago
A Gold Coast grande dame with an intimate vibe and personalized service, home to a lively brunch scene and pampering spa.
$100 resort credit.
Upgrade & extended check-in/out whenever possible.
The Hoxton Chicago
As much about the play as the stay, this Fulton Market favorite has a hotspot restaurant, bar and rooftop pool, plus supremely comfortable bedrooms.
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Things to do in Chicago, Illinois
Many of the comedians you see on SNL came through Chicago. Catch a show at the famous Second City or my personal favorite, Zanies. They are both located in the neighborhood of Old Town. I suggest grabbing dinner at Topo Gigio before or after your show and order the Conchiglie alla Sarda pasta. You'll thank me later!
Color Factory Chicago - Located in Chicago's Willis Tower (formerly Sears Tower), the Color Factory is an art museum with 16 immersive exhibits fun for all ages.
Walk or bike along the lakefront. Depending on the time of year you visit, the lakefront provides one of the best views of Chicago's skyline. I suggest renting Divvy bikes and riding up to Theater on the Lake where you can sit and enjoy a cocktail with a view.
Go to a concert. As one of the largest US cities, Chicago is lucky to have artists visit year around. In the summertime, Windy City Smokeout, Pride in the Park and Lollapalooza are the most popular, but if you are here during the winter months, catch a show at The Riviera, Concord Theater or the Aragon Ballroom. The indoor architecture of these old venues won't disappoint.
Go to a sports game! If you didn't already know, Chicago is home to the Cubs, White Sox, Bears, Bulls and BlackHawks, making it a huge sports town. Whether you are a fan or not, enjoy a baseball game at the iconic Wrigley Field. Prefer to tailgate? Soldier Field is the place for that!
A note from Artemis
You’ll need a Ventra card to ride public transportation. You can buy one online, at any train stop or at various shops.
Places to eat & drink in Chicago, Illinois
Places to eat in Chicago
Giant - Located in Logan Square, Giant has a seasonal American menu that keeps me coming back for more. My favorite items include the jalapeño biscuit, sweet and spicy peppers with anchovy bread and the saffron tagliatelle with crab.
Sushi by Bou - There are three locations in Chicago, but my favorite is the tiniest, located inside the West Loop's Emily Hotel. Reservations are required for this Omakase experience. Sushi feast while you listen to 90s Hip Hop. Need I say more?
Duck Duck Goat - Celebrity Chef Stephanie Izard's creative Chinese fare. Eat comforting Chinese favorites, such as Scallion Pancakes and Crab Rangoon in a vibrant atmosphere.
Elina's - An intimate space with fine Italian cooking! Make sure to reserve well in advance, because it seats less than 50 people. Order the Chicken Parmesan, Rigatoni all Vodka and Angel Hair Scampi.
Andros Taverna - The best Greek restaurant in the city - trust me I'm Greek! The spreads for the table and the Octopus are the standouts here.
Chicago Pizza & Oven Grinder - Modeled after a British pub, this no-frills pizza joint is not where you will find traditional or deep-dish pizza. They are known for their Mediterranean bread (to die for) and their pizza pot pies. Come hungry because the portions are huge!
Time Out Market - Perfect for a quick bite for lunch, Chicago's Time Out Market features a rotation of restaurants with chef-driven eats & cocktails with communal seating.
Places to drink in Chicago
Blind Barber - Hidden inside a West Loop barber shop, Blind Barber is a barber shop by day and a cocktail lounge by night. If you are looking for good cocktails and dancing, be sure to check it out!
Lazy Bird - Located in the basement of the Hoxton hotel, Lazy Bird is a popular late-night speakeasy with live music. There is typically a line to get in so get there early.
Mom's Place - My favorite dive bar in the city. Located in River North, Mom's Place is a karaoke bar on one side and hosts live music on the other. Enjoy cheap drinks and a song or two at Mom's!
Nights & Weekends - Funky bar in the West Loop. Cool vibes, good music and a DJ with a large dance floor in the back.
Cindy's Rooftop - For a classier vibe with a view of Millenium Park, visit Cindy's at the top of the Chicago Athletic Association hotel.
Need to Know
If you enjoy the food scene while traveling, check out my Foodie's Guide to Paris, France.
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