CHICAGO, IL
Chicago, IL, is known for its frigid winters and gorgeous summers. Nestled along Lake Michigan, the city offers waterfront views alongside towering skyscrapers. Its spunky street art flows throughout the city and there are enough attractions and incredible restaurants to keep you busy for days. My friend Jeremy is from Chicago and still lives there today. He shared his favorite spots in this guide. Also thank you to my friend Paige who added a few picks as well. Happy Traveling!
Travel Tip:
- Chicago is laid out in a grid system that makes it easy to know where you are as a first-timer. The lake is always East in case you get lost. Pull up your maps app and you can easily find your way on the reliable bus and train system
- If you want to climb up one of the skyscrapers for a view, make your way to the Signature Lounge in the John Hancock building. Instead of paying $35 to get a ride of the Sears Tower (nobody calls it the Willis Tower) ride up to the Hancock’s 95th floor for free and spend that money on a signature cocktail with an equally extravagant view. The best view is rumored to be in the woman’s bathroom…
One fun thing:
- Navy Pier offers a free fireworks show every Wednesday and Saturday night. Find a spot near the beach or at Navy Pier itself for a budget-friendly spectacle.
- AirBnB: AirBnB is probably the way to go in Chicago. There are plenty of offerings all over the city.
- Museum Campus: take your pick of several world-class museums all packed onto one convenient campus. There is something to suit everyone’s interests including the Art Institute of Chicago, Adler Planetarium, Shedd Aquarium, and The Field Museum. Jeremy’s favorite is the Adler Planetarium for interesting space exhibits. A curious visitor can easily knock off two incredible hallmarks in a day. An additional bonus is that they are all located on the water with excellent skyline views for candid or not so candid photos.
- Cubs Game at Wrigley Field: considered the Mecca of baseball and home of the lovable losers who finally won a World Series in 2016. The area has been transformed into a unique ballpark experience and you can expect the local bars to be lively before and after home games. The stadium itself is small and historic in a somewhat residential neighborhood. Ask anyone who has ever attended a game at Wrigley and they will tell you that the most unique part about it is that Cubs games are always at full capacity. Most of their games are during the day.
- Catch a concert on Northerly Island or Millenium Park: Chicagoans love to be outside during the summer, partly to make up for four months of frigid winter. That’s why the city hosts their concerts outside. Northerly Island hosts concerts with a picturesque view of Chicago’s skyline and lake. Lollapalooza Music Festival takes place in Millenium and Grant Parks which are sandwiched between the skyline and the lake. Also in Millenium Park, you’ll find the famous bean sculpture, skating rink in the winter and other exhibitions.
- Oak Street & North Avenue Beach: spend a summer day on Chicago’s famous beaches and you may even think you’re in Miami. People do not realize how large Lake Michigan is and how beautiful the beaches of Chicago are. Beach volleyball is a popular choice along with renting a Divvy Bike for a ride along the lakeshore
- Attend a Neighborhood Street Festival: Chicago is a city of neighborhoods, many named after distinct ethnic groups that originally settled there to create unique communities. Greektown, Chinatown, Ukrainian Village, and Pilsen (now predominantly Mexican after being settled by Czechs and Germans) are great examples of Chicago’s vibrant cultural centers. These neighborhoods take turns hosting the rest of the city’s inhabitants every summer with live music, local vendors, and authentic food options. This is the best way to explore Chicago’s neighborhoods and experience a new culture.
- Intuit: Center for Intuitive and Outsider Art: a funky museum not in the Museum campus. It features non-traditional, non-mainstream and self-taught artists. One main exhibit is “Jerry’s Map” where artist Jerry Gretzinger constructed an imaginary world landscape square-by-square starting back in 1963. He continues to add to it today.
- Second City show: go see a show where notable SNL personalities got their start. There’s usually an early evening show and late night show. On the weekends there’s also a matinee. You can order drinks and food to your seat. They also offer classes if you want to give it a go too!
- Wicker Park: walk around this hipster neighborhood and explore the records and vintage stores. Kokorokoko is a favorite vintage spot and Dusty Groove is a great records store.
- Palace Grill: a classic diner just a few blocks East of the United Center where catching local sports icons is the norm. This isn’t your hipster brother’s local spot for exotically sourced coffee, but rather a spot where the Blackhawks order their pre/post practice meals of generous omelets, hot skillets, and pressed sandwiches. It’s located near the Museum Campus, so it’s the perfect stop before spending a day exploring museums.
- The Bongo Room: a trendy but casual restaurant where sweet carbs are a must. Expect the guests around you to be snapping pictures of their decadent breakfast choices to send to their envious friends. If you have time and stomach space to indulge in over-the-top pancake and french toast creations, go to the Bongo Room. Jeremy recommends leaving plenty of time before your meal as the wait can be long and after as the food coma hits hard.
- Manny’s Cafeteria & Delicatessen: a Jewish deli that’s frequented by the locals. They serve a full breakfast on top of all of your Jewish favorites like hot pastrami, corned beef, and matzah ball soup. This family-owned spot is one of the few remaining Jewish establishments outside of the far North side. You’ll need to navigate the local old-timers and large construction crews here, but Manny’s will forever go down in Chicago history as the meeting place of Chicago’s greasiest political cronies that gave Chicago its political reputation.
- 3 Arts Club Café: the café in a posh and opulent home goods store. Along with being a home goods store, it’s home to a wine bar and a stunning lounge courtyard area. The coffee here is tasty and they have a wonderful full breakfast/brunch menu too.
- Shokolad: sits in Chicago’s Ukrainian Village neighborhood and the best place to sit down for a casual lunch of hearty Varenyky (dumplings) and Borscht. They offer non-Ukrainian food too if you’re not feeling adventurous. You’ll feel like you’re in a traditional yet contemporary European cafe where locals love to gather and converse. To finish off your experience, make your way to the fresh tort display for out-of-this-world desserts such as their ‘Spartak’ or ‘Napoleon’ cakes.
- Small Cheval: smaller less touristy versions of Au Cheval in cool neighborhoods. Au Cheval is on every publication of ‘must try’ burgers around the United States, but a local pro tip is to try its little siblings in Wicker Park or Old Town to avoid a three-hour wait. The classic Cheeseburger is a close replica of its famous big brother and will leave you with all of its satisfying guilt along with the rest of your evening to check out other attractions.
- Al’s #1 Italian Beef: a small unassuming sandwich shop with an incredible Italian Beef sandwich. Jeremy insists that the original location on Taylor Street is the only way to go. This signature Chicago sandwich is the perfect place to stop before making your way down Roosevelt to the museum campus. Try a Chicago-style beef sandwich with giardiniera. If you want to get it the way the locals do, ask for it to be baptized which means the sandwich is dunked and “baptized” in all the juices.
- Heaven on 7: a super secret hole-in-the-wall Cajun food restaurant for a spice lover. They are cash only and located on the 7th floor of a financial district building. It looks very unassuming. Inside, you’ll find a hot sauce wall and that the tables are covered in hot sauce.
- RPM Steak: as the city that was once the center of America’s meatpacking industry, a proper steakhouse belongs on this list. RPM is where Chicagoans go to splurge on the best cuts of meat there is to offer. Prepare to spend top dollar but the cocktails and fine dining are worth it. You’ll occasionally see a famous face too. It goes without saying, but order steak, not pork chops or anything else.
- Pequod’s Pizza: Locals will tell you that true Chicago-style pizza is a cracker crust tavern-style pizza cut into squares (try Vito & Nicks if you’re looking for that style), but since the word is out on deep dish, Pequod’s is the way to go. The big three names in deep dish are Giordano’s, Lou Malnati and Ginos, but Pequod’s is head and shoulders above the rest and their homemade fennel sausage is the best topping in the city. Pro tip – don’t get more than one meat on a deep dish to avoid too much juice sweating into the pie. If you’re looking for a vegan deep dish pizza, check out Kitchen 17.
- Green Street Smoked Meats: possibly the best barbeque the US has to offer outside of the South. Located in West Loop, this joint is surrounded by other great options as well as fantastic nightlife if you can survive the meat sweats. Their beef ribs are the length of your arm and champion a dark smokey bark that DIY smokers dream of. Also highly recommended are the sausage links and family-style sides.
- Girl & the Goat: a trendy Asian-inspired restaurant serving small plates that’s open 7 days a week. Stephanie Izard is the executive chef who was the first female chef to win top chef, an iron chef, and James Beard award winner. Get the green beans. Izard has a few restaurants in Chicago, but this is the favorite.
- Magnolia Bakery: if you find yourself shopping on Chicago’s infamous Magnificent Mile (the New York City 5th Avenue equivalent of Chicago), stop at Magnolia Bakery across the street from Macys. Take a leap of faith and order the banana pudding in a large serving to avoid going back for more – it’s that good.
- Donuts: Chicago is known for its delicious donuts. The big four spots are Stans, Do-rite, Firecakes and Doughnut Vault.
- West Town Bakery: a bakery with multiple locations including one across the street from Wrigley Field. Stop in for some cake balls or assorted cupcakes. A very popular choice for locals to bring into the office for birthdays and other celebrations.
- Rooftop Bars: Spend an evening in awe of Chicago’s amazing architecture on one of the many rooftop bars in and around The Loop. Cindy’s is always a crowd pleaser along with Avec and the London House.
- Old Town: This near North neighborhood is flooded with bar patrons looking for a fun night out. Jeremy’s personal favorites include The Vig where cookies are served at Midnight and the infamous Second City.
- Wicker Park: This neighborhood has a more hipster and eclectic social scene. Stop at Big Star for fantastic tacos and mezcals before making your way to Milwaukee Avenue to find cool bars and galleries.
