The Windy City, The City of Broad Shoulders, The Second City, Chi-town … one of my most requested city guides is finally here – Chicago! I’ve been living here for five years now and have seen the city change so much… restaurants have come and gone, the Cubs are now World Champions (what?!) but the pizza is still deeeeep. My friend Olivia and I decided to revisit all of our favorite spots over the past weekend to show you the best that Chicago has to offer! Chicago is situated on Lake Michigan, which gives the city an amazing beach-town feel in the summer filled with sailboats, BBQs, and hanging out along the lakefront. The prime time to visit the city is from June to September, and the favorite time of the year is October – when it’s a little brisk and the leaves start turning! Chicago can still be an exciting place in the winter but be warned that you’ll be bundled up pretty nicely and there might be just a little snow. Here are some hotels I’d recommend staying at:
- Thompson Hotel
- Public Hotel
- The Langham
- Soho House Chicago
- The James
- and for a more boutique stay, Hotel Lincoln.
- Cafe Ba-Ba-Reba! – Spanish tapas that’s great for big groups. my favorites: 43, 50, 30, 23, 32, 59, 62/52, 44
- Green Street Smoked Meats (West Loop) – My favorite BBQ in Chicago… maybe because it’s Texas-style 😀
- Girl & the Goat (West Loop)
- Little Goat Diner (West Loop)
- Au Cheval (West Loop) – Best burger in the city, but expect a long wait time!
- Hubbard Inn (River North)
- Sunda (River North)
- ēma (River North) – Light, California-inspired Mediterranean food. don’t forget the frozen Greek yogurt for dessert!
- Big Star (Wicker Park)- Best tacos with the best patio in Chicago. Doesn’t hurt that they a killer margarita and full whiskey bar, too!
- Drum Bar (Magnificent Mile) – my go-to cocktail bar, atop a boutique hotel
- Duck Duck Goat (West Loop)
- Crisp (Lakeview)
- Avec (West Loop) – The best Mediterranean
- Beatrix (River North/West Loop)
- Summer House Santa Monica (Lincoln Park)
- HUB 51 (River North) – breakfast nachos. enough said.
- Antique Taco (Wicker Park)
- Bongo Room (Wicker Park) – Indulgent brunch
- Parson’s Chicken & Fish (Logan Square) – The patio = Chicago summer. A few frozen negronis (their house specialty!) and hush puppies and I’m the happiest person
- Oiistar (Wicker Park)
- 25 Degrees (River North/Wicker Park) – If you’d like to brunch – and use it as a verb – they’ve got $10 bottles of champagne.
- Duck Duck Goat (Hong Kong-style Chinese)
- Longman & Eagle (Logan Square)
- Taxim (Wicker Park)
- Lonesome Rose (TexMex in Logan Square)
- En Hakkore (Bucktown)
- Lilly’s Q (Wicker Park)
- Aba (West Loop)
- Monte Verde (Italian in West Loop)
- Mott Street (Wicker Park) – Asian Fusion
- Stan’s or Donut Vault has the best donuts.
- Publican Quality Meats (West Loop)- The Chicken Parm #2 and Return of the Gyro might be the best sandwiches in Chicago. The new addition of their avocado salad is a great starter.
- Parachute (Logan Square) – Funky-chic place serving modern, creative Korean-American fare plus wine & cocktails.
ant (Logan Square) – Seasonal New American plates & craft cocktails are served in a funky storefront with local art
As far as Chicago deep-dish pizza goes, Pequod’s is my personal favorite… followed by Lou Malnati’s (on Rush St.!) — but my favorite pizza in town might be the cozy, underground BRICKS. The Sweet Heat with some Slutty Ravioli can’t be topped! To get your fix of the famous Chicago hot dog, check out Devil Dawgs!
- Buzz Killer Espresso
- Gaslight Coffee Roasters
- Caffe Streets
- Ipsento Coffee
- The Coffee Studio
- The Wormhole Coffee – retro-themed shop in Wicker Park serving up Halfwit coffee
- Big Shoulders Coffee – great grab-n-go in West Town
- Intelligentsia Coffee – the Old Town location is my neighborhood coffee shop!
- Sawada Coffee is right across from Soho House in the west loop and worth popping into.. get the Military!
- Violet Hour
- Maude’s Liquor Bar
- Lost Lake
- The Dawson
- Cubs game at Wrigley Field (try seeing a game from the Wrigleyville Rooftops!)
- Improv comedy show at Second City
- Chicago Water Taxi to Chinatown
- Garfield Park Conservatory
- Architecture Boat Tour on Chicago’s First Lady – It sounds dorky and touristy, but actually pretty awesome. This one is my favorite. If worst comes to worst, there’s a bar on board!
- Cloudgate (‘The Bean”) in Millenium Park
- Run/bike/walk along the Lakeshore Trail
- Enjoy the room at the Signature Room at the John Hancock Tower – pro tip: go up there and sit at a table. don’t order, but take photos from the windows but then bail and go to Drum Bar across the street for even better cocktails and a more private space!
- Shop along the Magnificent Mile
- The Museum Of Contemporary Art Chicago is one of the largest Post-WWII contemporary art museums in the country. The museum is filled with thought-provoking collections & installations and has hosted exhibitions ranging from Frida Kahlo to Jeff Koons. Located in Chicago’s Downtown.
- With PoetryMagazine as its flagship initiative, the not-for-profit Poetry Foundation was created to promote poetry to a wider audience. Its 30,000-volume library contains rare and original works of modern and contemporary poetry. Located in Chicago’s River North neighborhood.
- If you’d like a first-hand look at Chicago’s history, culture, and future, then make sure to stop by the Chicago History Museum. This engaging museum allows a peek into Chicago’s past. It houses many items and artifacts of Abraham Lincoln, including his deathbed, and even the clothing he and wife Mary Todd Lincoln wore the evening of his assassination. Located in Chicago’s Lincoln Park neighborhood.
- This landmark building was the nation’s first free municipal cultural center. The Chicago Cultural Center hosts rotating galleries of art exhibitions and installations. The most notable of these was when a then-unknown (and now world-famous street photographer) Vivian Maier’s work was first exhibited in the United States. Fun fact: the center is also home to the largest Tiffany Favrile stained-glass dome in the world, measuring 38 feet in diameter. Located in Chicago’s Downtown.
- Founded in 1903, the Adler Planetarium is America’s first planetarium. The building hosts three full-size theaters, intriguing intergalactic exhibits, and a collection of antique astronomy instruments. The Doane Observatory is the only place Chicagoans can view stars, planets, and celestial objects through the largest telescope in the Chicago area. It is located on Chicago’s Museum Campus.
- The Shedd Aquarium was the first inland aquarium with a permanent saltwater fish collection and, at one time, was the largest indoor aquarium in the world. The aquarium contains over 1,500 species of fish, marine animals, and amphibians. It is located on Chicago’s Museum Campus.
- One of the city’s most prominent museums, the Art Institute of Chicago is the second-largest art museum in the United States. The Art Institute houses impressive Impressionist and Post-Impressionist works in its permanent collection. The most notable pieces in the museum are a number of Claude Monet’s Haystacks and Water Lilies, Edward Hopper’s Nighthawks, Mary Cassatt’s The Child’s Bath, Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte, and the iconic American Gothic by Grant Wood. And who can forget Ferris Bueller’s famous visit to the museum in the 1986 film! Located in Chicago’s Grant Park.
- The architectural beauty that is the Field Museum was erected in 1921. The magnificent building is the focal point to Chicago’s Museum Campus, and it’s no wonder why as the site attracts more than 2 million visitors every year. The Field Museum is also one of the nation’s most premier natural history museums in terms of collection size and its educational programs. Inside of its rich walls lives SUE, the most complete and well-preserved tyrannosaurus rex fossil discovered to date.
I hope you found this guide helpful and informative! Please let me know if you are planning on visiting the city and have any other questions. Or recommendations! I know I couldn’t fit everything into here and sure I missed out on some great spots. Let me know if you’re an uber rider too ~ and if you used the ride request app to get around the city during your stay!
Photography by John & Wesley Taylor