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 sail boats, BBQs and hanging out along the lakefront. The prime time to visit the city is from June to September, and 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.
The city is pretty central and on a grid system, after the Chicago Fire of 1871. Chicago is a big city, but the layout makes it so easy to bop around. As I’m a car-less city slicker, Olivia and I decided to use uber over the weekend to get place to place. Honestly, you can get anywhere you need to get to in Chicago in such a short amount of time. I use the ride request app because it’s convenient, reliable and cheaper than a taxi! Also, it’s great to split the fare with friends so we went 50/50 on all of our rides around town. We hailed an uberX and were off – planning to take advantage of Chicago’s awesome food scene and the multitude of museums the city has to offer.
- 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)
- Au Cheval (West Loop) – Best burger in the city. Expect a long wait time, but
- 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)
- 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.
- Longman & Eagle (Logan Square)
- En Hakkore (Bucktown)
- Lilly’s Q (Wicker Park)
- Farmhouse (River North)
- 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.
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
- Bow Truss Coffee Roasters
- 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!
- 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
- Cloudgate (‘The Bean”) in Millenium Park
- Rent bikes or run along the Lake Shore 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
Olivia and I hailed quite a few uberXs over the weekend. Getting from one neighborhood to another in Chicago is the big hurdle, as once you get to Wicker Park it’s a pretty walkable place. I always feel safe in an uber. I have no qualms with getting into a stranger’s car because I know the uber driver-partner has been vetted and has a driver profile that is transparent. I can share my ride with friends or family to let them know where I am, plus… I wear my seatbelt.
- 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 he 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 Favril 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 it’s 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 Cassett’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 its 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 tyrannosaurs 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
This post was made in sponsorship with Uber. All opinions that I’ve expressed here are my own.