CHICAGO, UNITED STATES
Chicago is a metropolis made up of 77 distinct and vibrant neighborhoods - most of which are connected by the city’s impressive public transportation system. These diverse, individual pieces are what make the “Windy City” puzzle the greatest in the United States! A visit during the summer in particular will help you understand why so many people obsess over “Summertime Chi”. There’s no place like it! As incredible and beautiful as Chicago is, it is also one of the most systematically and historically segregated cities in the nation, leading news outlets to peg certain areas as “too dangerous” to visit. Speaking from personal experience, this could not be further from the truth. Chicago is exceptional because of the sum of its parts - not by the subtraction of any of them. I encourage you to visit as many different neighborhoods as possible to get a holistic view of this amazing city!
Attractions:
Chicago is broken down into four main areas - the Loop, North Side, West Side, and South Side. If you have the time, I recommend spending at least a day in each area to get a true feel for the city!
Highlights of the Loop (a.k.a. Downtown):
The Big Five: The five main attractions in the Loop are the Art Institute, Buckingham Fountain, Field Museum, Millennium Park, and Navy Pier. The Art Institute is one of the oldest and largest art museums in the United States, housing iconic pieces such as American Gothic, A Sunday on La Grande Jatte, Nighthawks, and more; entrance costs $25. Next, we have Buckingham Fountain, one of the world’s largest fountains standing just north of Grant Park, another tourist favorite. Just south of Grant Park is the Field Museum, an enormous natural history museum featuring the famous and giant T. rex named SUE; entrance costs $40. Fourth, we have Millennium Park, which is the most visited of the bunch due to its pretty landscape, sizable ice rink, and elaborate outdoor sculptures, including Cloud Gate (known locally as “The Bean”). Last but not least is Navy Pier with its 200-foot tall Ferris wheel. A sky-high ride costs $18, but walking around is free!
Lakefront Trail: This walking/cycling path is 18.5 miles long and a very scenic place to admire the skyline and lake!
Float on the Chicago River: One of the most popular tours in Chicago is the Architecture Boat Tour. The 90-minute narrated cruise explores all three branches of the river, passing all of the city’s grandiose architectural wonders along the way; tickets cost $48. For those with a tighter budget, you can always hop on the Water Taxi instead. One-way tickets cost $6 and day passes cost $10. I recommend a 25-minute voyage down to Chinatown for a delicious meal and to see Ping Tom Memorial Park!
Skydeck Chicago: Visitors can climb up the Willis Tower for a commanding, 1,350-foot view of city; tickets cost $35.
Oak Street Beach: A great place to lay out and catch some rays while taking in the surrounding sky-scrapers. No alcohol is allowed (Thanks, Obama).
Highlights of the North Side:
Wicker Park & Logan Square: These hipster parts of town are full of street art, dive bars, and chic cafes. You’ll find the 606 here as well, a beautiful 2.7-mile long walking trail for walkers, joggers, and bikers. Wicker Park in particular is home to my favorite restaurant and rooftop bar in the city (Handlebar and The Robey respectively). Paradise Park and Estereo are two noteworthy spots for cocktails!
Lincoln Park: If you’re looking to experience Chicago nightlife, I recommend spending an evening out and about here! Home of DePaul’s college campus, Lincoln Park is a fun area where you’ll find lots of young people and free attractions, such as North Avenue Beach, Lincoln Park Conservatory, and Caldwell Lily Pool!
Lakeview: If you have the chance to stop by Wrigley Field for a Cubs game, you will not regret it. They’re an absolute blast! Within Lakeview, you will also find two of the liveliest areas in the city (Boystown and Wrigleyville). Be sure to pencil in a night out here!
Highlights of the West Side:
Humboldt Park: Chicago is full of vast green spaces, but my favorite has to be Humboldt Park! This huge park has tennis and basketball courts, gardens, a batting cage, and even a pond! Visitors can float on the water on swan boats here for $11/hour. Be sure to also stop by Atmos Coffee Shop, a Black- and Latina-owned café!
East Garfield Park: Having a place to visit regardless of the time of year is very important in a city like Chicago! Snow or shine, you will find one of the nation’s largest botanical conservatories here, Garfield Park Conservatory. With many rooms housing different types of plants and flowers, you will not be disappointed! Stop for lunch beforehand at Inspiration Kitchens, a restaurant dedicated to training Chicagoans combatting homelessness.
Little Village: La Villita, or South Lawndale, is a predominantly Mexican neighborhood on Chicago’s southwest side. Full of shopping (Little Village Discount Mall) and incredible food (Mi Tierra & La Catedral), you can easily spend a day exploring here!
Highlights of the South Side:
Hyde Park: If you visit Chicago in the spring, make a beeline for Jackson Park to witness the gorgeous cherry blossoms! While you’re here, make time for the Museum of Science & Industry - one of the nation’s biggest and oldest museums dedicated to technological advancements and scientific exploration; tickets cost $22. For a picturesque stroll or picnic, I recommend both Promontory Point and Midway Plaisance Park.
Bronzeville: Coined as Chicago’s “Black Metropolis”, this neighborhood is one of the city’s most celebrated and historic cultural hubs, featuring famous residents such as Ida B. Wells, Gwendolyn Brooks, and Louis Armstrong. When you visit, be sure to check out DuSable Museum of African American History, which is free to enter. For food and dessert, stop in Peach’s and Shawn Michelle’s Homemade Ice Cream respectively! Just south of Bronzeville’s 51st Street border, you will also find Washington Park, containing the Fountain of Time.
Bridgeport: I would be remiss if I didn’t mention the home of the White Sox, Guaranteed Rate Field. Tickets will be much cheaper than a Cubs game with the additional perks of summertime fireworks, $1 Hot Dog Wednesday Nights, and Craft Kave, a bar in right field with more than 75 types of beer. After the game, be sure to grab a drink at the one-of-a-kind Maria’s Community Bar!
Other things to check out include: Chicago Theatre, Museum of Contemporary Art, Chicago Cultural Center, Lincoln Park Zoo, Frederick C. Robie House, Magnificent Mile, North Branch Bike Trail (45 minutes NW of Chicago), Bahá’í House of Worship (1 hour N of Chicago), and Devil’s Lake State Park (3.5 hours N of Chicago).
Accommodation:
Hotel - Palmer House: This 4-star hotel is timeless. Part of the Historic Hotels of America, it was the first hotel in Chicago with elevators. In fact, prior to March 2020, it was thought to be the longest continuously operating hotel in North America! Today, the Palmer House boasts award-winning dining with a beautiful spa and health club. It is located in central downtown, less than 10 minutes on foot from the Art Institute, Buckingham Fountain, and Millennium Park.
Hostel - Getaway Hostel: Located in Lincoln Park, this hostel is where the fun is! Their kitchen is well-equipped and their patio/terrace is gorgeous. Backpackers will enjoy the neighborhood vibes here and all of the main attractions downtown are just a quick 15-minute train ride on the brown or red line!
Transportation:
Chicago’s metro system, known as the “L”, is one of the oldest and largest transportation networks in the United States. It is one of my favorite assets of the city as it stretches over 100 miles and connects much of Chicago together. There are 8 lines in total, two of which run 24/7 (blue and red lines). One-way tickets cost $2.50 and day passes cost $10, although I find the day passes are often not worth it since transfers only cost $0.25. Visitors will also need to purchase a “Ventra” card, which costs $5; transit value can be added at nearly every metro station. Another great way to get around the city is via the public Divvy bikes. Bikes cost $3.30 for 30-minute rides, or $15 for 24 hours.
Chicago’s main train station is Union Station; all trains below leave from here. The main bus stations correspond to the two bus companies servicing the region - Greyhound (station here) and MegaBus (station here).
Milwaukee is 45 minutes by airplane from Chicago and costs $140-$190 depending on the time of the year (on United or American). The bus ride is 2 hours and costs $17. The train ride is 1.5 hours and costs $25. By rental car, the drive from Chicago to Milwaukee is 1.5 hours.
Nashville is 1.5 hours by airplane from Chicago and costs $65-$120 depending on the time of year (on United, American, or Spirit). The bus ride is 11 hours and costs $65. The train ride is 11 hours and costs $100. By rental car, the drive from Chicago to Nashville is 7 hours.
Washington, D.C. is 2 hours by airplane from Chicago and costs $80-$125 depending on the time of year (on United, American, or Spirit). The bus ride is 18 hours and costs $60. The train ride is 17.5 hours and costs $84. By rental car, the drive from Chicago to Washington, D.C. is 12 hours.
Denver is 2.5 hours by airplane from Chicago and costs $60-$200 depending on the time of year (on Frontier, United, or American). The bus ride is 20.5 hours (indirect; via Des Moines) and costs $117. The train ride is 18.5 hours and costs $159. By rental car, the drive from Chicago to Denver is 14.5 hours.
Badlands National Park is 3.5 hours by airplane and car from Chicago. The flight from Chicago to Rapid City (South Dakota) is 2.5 hours and costs $300 (on United or American). The drive from Rapid City to Badlands is 1 hour. By rental car, the drive from Chicago to Badlands is 12 hours.
Chicago’s two airports are both a quick train ride from downtown. O’Hare (ORD) is 15 miles NW of the city center and is accessible via the blue line (45 minutes; $2.50). Midway (MDW) is 10 miles SW and is accessible via the orange line (30 minutes; $2.50). The blue line runs 24/7, while the orange line runs from 1:30am-3:30am; trains depart every 15-30 minutes.
