- The country’s 3rd largest city
- Widely renowned for its impressive architecture
- Rich history and culture
Metro Population: 9.5 million (#3 in the U.S.)
When To Visit: April-October
Climate: Very seasonal – with a hot summer, cold snowy winter, and cool spring and fall
The largest city in the Midwest, Chicago is situated on giant Lake Michigan and centered around The Loop, the city’s downtown area. Striking modern architecture, an endless array of cuisines, and probably the best rail system outside of the East Coast make it a very exciting and practical city to visit.
Photo: Millennium Park Ampitheatre
Where To Go in Chicago
- Millennium Park: The crown jewel of Chicago, this stunning park opened in 2004 and features a large walk-in fountain area, beautiful gardens, a modern concert venue, and the famous Cloud Gate sculpture more commonly known as “The Bean.” Free.
- Buckingham Fountain: This beautiful fountain just a short walk from Millenium Park has great views of the water and the downtown skyline. Free.
- Chicago River: A walk along this river in the center of the city provides incredible views of the Chicago’s architecture. If you’re able to splurge on a $35 ticket for the most affordable of the city’s many architecture boat tours, it’s completely worth it for the grand views and fascinating history you’ll experience.
- Willis Tower: This is it – the tallest building in the country! A $23 ticket gets you to the SkyDeck, where you can sit in an unsettling/epic glass box thousands of feet above the city.
- Hancock Tower: Looking for an epic view for free? Head to the 96th floor Signature Lounge in this also tall tower and soak in breathtaking views of Lake Michigan and Chicago, perhaps ordering a drink or dessert. Free.
- Navy Pier: Take a stroll down this recently renovated pier which has museums, food, and a ferris wheel. Don’t miss the free Stained Glass Museum. Free.
- Jane Addams Hull House Museum: If you’re someone who aims to make a positive difference in the world, you’ll love learning about how Jane Addams did just that – advocating for low-income people and against child labor over 100 years ago – in this free museum just outside The Loop. Free. 800 Halsted Street. (312) 413-5353.
This upscale neighborhood north of The Loop has beautiful homes at which to gawk and plenty of food and shopping options.
- North Avenue Beach & Lakeshore Path: A walk along Lake Michigan is a must while you’re in Chicago and this popular beach is one of the best starting points – you’ll get great views of the lake and the city. If it’s a hot day, you can pretend you’re in California and get some sunbathing in. Free.
- Lincoln Park Zoo: Chicago’s zoo is free! It’s on the small side, so it’s easy to take a pleasant walk through.
Wrigleyville & Boystown
The North side of the city is home to the Cubs’ Wrigley Field (and countless surrounding sports bars) and Boystown, the city’s lively gay epicenter.
Bucktown, Wicker Park, & Logan Square
These trendy neighborhoods on the Blue Line are popular hotspots for locals and have some of the city’s best food and bars.
- City Lit Books: This cute independent bookstore is a joy to explore. Free. 2523 North Kedzie Boulevard, Logan Square. (773) 235-2523
- Humboldt Park: One of the city’s larger open spaces, this peaceful park has a large lake and several gardens. Free.
Chicago Cheap Eats
Chicago restaurants and fast casual eateries popular with locals where you can get a full meal for under $15. I always highlight some vegan or vegetarian options – cutting down on the amount of meat you eat is by far the #1 way you can reduce your environmental impact and contribute less to animal cruelty.
Irazu: Enjoy the unique flavor of Costa Rican cuisine at this casual and affordable cash-only eatery. Make sure to try their oatmeal shake! 1865 North Milwaukee Avenue, Bucktown. (773) 252-5687
Lou Malnati’s: Locals’ favorite deep dish pizza spot, this is the best place to try Chicago’s iconic dish. There are locations throughout the Chicago area, including this one near the city center. 439 North Wells St, The Loop. (312) 828-9800
La Bomba: You’ll find super cheap and authentic Puerto Rican food at this small homey restaurant with a to-go counter and table seating. I recommend any of their plantain sandwiches. 3221 West Armitage Avenue, Logan Square. (773) 394-0106
Rio’s D’Sudamerica: This extravagantly decorated Peruvian restaurant has beautiful art and dramatic high ceilings. For such an elegant place, the food is reasonably priced. Closed Mondays. 2010 West Armitage Avenue, Bucktown. (773) 276-0170
Jeni’s Ice Creams: Creamy, luscious scoops of ice cream in a variety of fun flavors. There are three locations in the Chicago area. 1505 North Milwaukee Avenue, Wicker Park. (872) 802-4668
Chicago bars, lounges, and clubs that are popular with locals and meet one or more of these criteria: A) Unique, unlike anyplace you’ll find in another city B) Fun and lively, sure to be a good time C) Beautiful decor or view
Replay: This small gay arcade bar in the heart of Boystown has FREE arcade games and a cool backyard patio and bar. 3439 North Halsted Street, Boystown. (773) 661-9632
Cindy’s: This popular rooftop bar has the best possible views of Millennium Park and a classy vibe without terribly high drink prices. 12 South Michigan Avenue, The Loop. (312) 792-3502
3 Dots and a Dash: Love cute fancy cocktails? This island-themed bar has dozens of unique tropical drinks in a festive setting. 435 North Clark Street, The Loop. (312) 610-4220
Roscoe’s: One of the city’s largest gay clubs, this popular multi-level venue is a great spot to dance and has reasonably priced drinks. 3356 North Halsted Street, Boystown. (773) 281-3355
Nearby Side Trips from Chicago
Indiana Dunes National Lakeshore: Just an hour east of the city, this beautiful slice of coastline has tall dunes, thousand of native plants, and great hiking trails.
Starved Rock State Park: Easily Illinois’ most popular nature destination, this park 2 hours south of Chicago has stunning waterfalls, 18 moss-covered stone canyons, and peaceful views of the Illinois River.