Chicago, Illinois is the third most populous city in the U.S., behind New York City and L.A. and home to almost 10 million people. Nicknamed ‘The Windy City’, Chicago is situated along the Southwestern shores of Lake Michigan. While the bustling downtown area (the Loop), with its many skyscrapers is architecturally rich and artistically infused, the best way to see the city is to visit its many neighborhoods. With so many options for what to see and where to go, getting advice from a local is essential before planning your trip. Check out our interview with local, Patrick, for help planning a weekend getaway or a vacation to this amazing city!
THE LOCAL: Patrick
WHY YOU SHOULD TRUST HIM: 30 year old Patrick has lived in the City of Chicago for 12 years, loves to eat and drink at the newest restaurants and bars in the city, and is constantly trying to see and do all that Chicago has to offer.
1. Favorite Street to Wander/Stroll in Chicago?
Wicker Park– Damen/Milwaukee at the “6 Corners” intersection. I’d recommend walking south from Damen & Willow to North Ave/Milwaukee/Damen, then southeast on Milwaukee to Ashland & Division, then back west on Division towards Damen. This is easily the hottest area of Chicago right now.
2. Best Coffee Shop?
I don’t drink coffee, but I’ve heard Dark Matter coffee in the Ukrainian Village/Humboldt Park is great. My favorite all in one place (food, groceries, beers, coffee, etc.) is definitely the Whole Foods on Kingsbury. This will appeal to anyone and shouldn’t be missed by someone who has never been, in my opinion. I know it’s not super original, but there aren’t many other Whole Foods like this except for a couple being built in California and at their headquarters in Austin.
3. Best Area to Shop Local?
Armitage/Halsted in Lincoln Park is a classic shopping neighborhood with less hustle than Michigan Avenue (and more boutique shops). A bit further north and west is the Southport corridor, which offers a long stretch of big brand stores and local boutiques. The Damen/Milwaukee route above is another best bet, and Randolph/Fulton streets in the West Loop offers great shopping plus the most original, up-and-coming restaurants.
4. Favorite Sunny Day Agenda?
Take the Lakefront path for a run or bike ride. The Northbound route is quieter, and while the Southbound route is busy, it offers more scenic Chicago views. Then grab some of best tacos in the city on the Big Star patio in Wicker Park, followed by dinner on an awesome garden patio at Piccolo Sogno. Not done eating and drinking yet? Head to after dinner drinks at the Violet Hour. Another cool spot to check out in Bucktown is the 606, a newly-opened walking & biking path created on an old railroad track. It connects to six neighborhood parks at ground level and features art installations and other amenities. The name comes from the 606 zip code prefix Chicagoans share. (Psst: this is similar to the Highline in New York). After a stroll along the 606, head to Small Cheval for an award-winning burger & a hoppy IPA.
5. Most essential Chicago Tip?
Bring your appetite and be sure to make an advance reservation at one of the must-visit Chicago restaurants. If you’re up for public transportation, the “L” is a great option to get around and is fairly easy to navigate. If you’re confused by which direction to go or which line to use, just ask someone walking by- most Chicagoans are very friendly!
TRIPADVISOR’S TOP FIVE CHICAGO ATTRACTIONS
1. Art Institute of Chicago– Thumbs Up. Consistently an awesome experience.
2. Cloud Gate– Debatable. If you really want to see Millenium Park, you’ll be amidst throngs of other tourists clamoring for an unobstructed picture of the “Bean’s” reflection. Go early and bring your camera for a quick snap, then stroll through the rest of Millennium Park or head to the Art Institute.
3. City Tours- hmmm…I’d give Architectural Boat Tours a Thumbs Up. Make sure to check in advance whether or not your boat will have a bar on board. If not, secure drinks from the kiosk before departing.
4. Millennium Park– Same with Cloud Gate (debatable). If you want to see a park/huge tourist attraction, this is it. By no means should you ever substitute this with Navy Pier – HARD PASS! On a nice day though, the Park can be a great time and offers plenty of free attractions and lots of interesting public art. With the newly opened Maggie Daley park, I’d say a visit to Millennium Park is worth your time. Stop by the park to enjoy the climbing wall, tennis courts, and gardens; plus in the winter, an ice skating rink!
5. Museum of Science and Industry– Thumbs Down. Only go if there’s a must-see exhibit or you cannot come up with something better to do…which is difficult in this city! The location is undesirable (far south and away from everything else) and for those on shorter trips to Chicago, this excursion cannot be justified. Instead, check out one of the many summer street festivals in the city- there are usually quite a few to choose from in various neighborhoods and can be a nice alternative to spending your whole day inside museums (plus, there’s usually good food and drink carts!)
TRIPADVISOR’S TOP FIVE CHICAGO RESTAURANTS
1. Alinea– Thumbs Up.
Major caveat: you’ll need to purchase tickets months in advance and be prepared to spend upwards of $350 per person (without drinks) for what is arguably the best meal in the US. As of summer 2016, Alinea recently underwent a full-scale renovation to modernize the space and to stay at the forefront of Chicago’s three star Michelin restaurants. If that’s not quite up your alley, visit Blackbird instead.
2. Bavette’s Bar and Boeuf– Thumbs Up.
In my opinion, the best steakhouse in the city, which is quite the accomplishment considering there are so many good ones- and mediocre ones- in Chicago. Go big and order the prime cuts if available. Again, this spot requires a reservation waaaay in advance.
3. Mexique– Thumbs Down.
4. Joe’s Seafood, Prime Steak & Stone Crab– Thumbs Down.
Good food, but nothing special. You won’t find me making a reservation here with all the other brilliant meat/seafood joints the city has to offer.
5. Momotaro Restaurant– Thumbs Up. Wayyyy up.
This place ROCKS. It’s huge, fancy, exciting, and pushes your comfort levels to new heights. Momotaro is also extremely popular and requires an advance reservation.
Are you a Chicago local? Would you add any attractions or restaurants to our list? If so, let us know in the comments below!