Chicago is the Midwest’s indisputable capital — a city of 2.7 million people on the southwestern shore of Lake Michigan with world-class architecture, the Art Institute, deep-dish pizza, legendary blues and jazz, and a lakefront trail system that makes it one of the most livable large cities in America. The El train running through the Loop is the most cinematic urban transit experience in the country.
Chicago: The Midwest’s Undeniable Capital
Architecture, the Lake, deep-dish, and the blues.
I have a confession: I have never been able to stay away from Chicago for more than a few months at a time. There is something about the way the skyline hits you as you drive north on Lake Shore Drive, the wind carrying the smell of Italian beef from a stand you cannot quite see, the low rumble of the ‘L’ overhead — it grabs you and does not let go. Chicago is not just a great Midwest city. It is one of the great cities on Earth, and I will argue that with anyone.
Why Chicago Belongs on Your List
Every major American city makes grand promises. Chicago actually delivers. You get world-class art, a food scene that punches well above what coastal snobs expect, live music on any night of the week, and 26 miles of public lakefront that feels like an ocean shore. The architecture alone is worth the trip — this is the city that essentially invented the skyscraper, and it wears that history like a badge of honor on every block.
What sets Chicago apart from, say, New York or LA is the attitude. People here are friendly without being performative about it. A bartender in Logan Square will genuinely want to know where you are from. The guy running a taco cart in Pilsen will tell you exactly which salsa is going to wreck you. It is a big city with a small-city heart, and that is rare.
Where to Eat (and What to Order)
Let me be direct: if you come to Chicago and only eat deep-dish pizza, you have missed the point. That said, you absolutely must eat deep-dish pizza.
Lou Malnati’s (multiple locations) is my go-to. The Malnati Chicago Classic with its buttercrust runs about $16-22 for a small, and it is worth every cent. Pequod’s in Lincoln Park does a caramelized-crust version ($18-24) that inspires genuine devotion. Skip Giordano’s — it is fine, but it is the tourist default and you can do better.
For Italian beef, Al’s #1 Italian Beef on Taylor Street ($8-12) is the original. Order it dipped with hot giardiniera. If you order it dry, I will not judge you, but I will be quietly disappointed.
Girl & the Goat in the West Loop (entrees $18-36) is Stephanie Izard’s flagship and remains one of the best meals in the city. Reservations fill fast, so book two weeks out. For something more casual in the same neighborhood, Au Cheval does a double cheeseburger ($16) that has ruined all other burgers for me. Expect a 90-minute wait on weekends — put your name in and grab a drink at the bar next door.
In Pilsen, walk down 18th Street and stop at Don Pedro Carnitas for tacos ($3-4 each) that will make you question every taco you have eaten before. Mi Tocaya Antojeria (small plates $12-22) elevates Mexican cuisine without losing its soul.
For a splurge, Alinea (tasting menu $250-350) remains one of the best restaurants in the world. It is an experience, not just a meal. Book months in advance.
Neighborhoods Worth Your Time
The Loop & Magnificent Mile — This is tourist central, but for good reason. The Art Institute of Chicago ($25 general admission, free for Illinois residents on certain days) is genuinely one of the best art museums on the planet. Spend a full morning here. Millennium Park is free and the Bean (officially Cloud Gate) is actually more impressive in person than in photos. Walk the Riverwalk at sunset and grab a drink at City Winery on the river ($12-18 glasses).
Wicker Park / Bucktown — This is where Chicago’s creative energy concentrates. Vintage shopping on Milwaukee Avenue, cocktails at The Violet Hour ($15-18 drinks, no sign on the door — look for the light), and late-night eats at Big Star (tacos $4-6, excellent whiskey list). If you are here on a weekend morning, the line at Dove’s Luncheonette ($14-20 brunch plates) is worth enduring.
Lincoln Park / Lakeview — Lincoln Park Zoo is completely free, which is remarkable for a zoo this good. Wrigleyville gets rowdy on game days — catch a Cubs game at Wrigley Field ($25-80 for bleacher seats) even if you do not care about baseball. The atmosphere is the point.
Hyde Park — The South Side does not get the tourist traffic it deserves. The Museum of Science and Industry ($21.95) could occupy an entire day. The University of Chicago campus is gorgeous, and Valois Cafeteria ($8-14) is a cash-only institution where Obama used to eat regularly.
Pilsen — Chicago’s vibrant Mexican-American neighborhood is packed with murals, galleries, and some of the best food in the city. The National Museum of Mexican Art is free and excellent.
The Lakefront
I cannot overstate this: Chicago’s lakefront is the city’s greatest asset. The 18-mile Lakefront Trail runs from Ardmore to 71st Street and it is spectacular for running, biking, or just walking. Rent a Divvy bike ($3.30 for a single ride, $16.50 for a day pass) and ride from Navy Pier south to the Museum Campus. On a clear summer day, with the skyline to your left and Lake Michigan stretching to the horizon on your right, you will understand why Chicagoans are so fiercely loyal to this city.
North Avenue Beach has a vibe somewhere between Miami and a neighborhood block party. Montrose Beach is more chill and has a great bird sanctuary.
Pro Tips from Countless Visits
The Chicago Architecture Foundation Center River Cruise ($47) is genuinely the single best activity in the city. I have done it four times and learn something new each time. Book through the architecture center, not the generic boat tours.
Second City ($30-55) in Old Town is where most of your favorite comedians got their start. The improv shows are consistently excellent. Go on a weeknight for smaller crowds.
For blues, skip the overpriced tourist joints on the north side. Buddy Guy’s Legends in the South Loop ($20 cover on weekends) is the real deal. Rosa’s Lounge in Logan Square is smaller, grittier, and might be my favorite live music venue in the city.
Scott’s Tips for Chicago
Getting There: Fly into Midway if you can — it is smaller, less chaotic than O’Hare, and the Orange Line gets you downtown in 25 minutes. If you drive, budget $40-60/day for parking downtown and consider leaving the car at your hotel.
Best Time to Visit: June through September is peak season and for good reason — the city comes alive with street festivals nearly every weekend. May and October offer fewer crowds and pleasant weather. Winter is brutal but hotel prices drop 40-50%, and the holiday markets are legitimately charming.
Getting Around: The CTA is excellent. Buy a Ventra card at any station. For most visitors, a 3-day pass ($20) covers everything. Uber and Lyft are plentiful but surge pricing hits hard during rush hour and after events. Chicago is one of the most walkable cities in America — if you are staying in the Loop, you can reach most major sights on foot.
Budget Tips: Many museums offer free days — check schedules before your trip. The Lincoln Park Zoo is always free. Eat your big meal at lunch; many high-end restaurants offer lunch specials at half the dinner price. Chicago dogs from a street cart ($3-5) are a perfectly legitimate meal.
Safety: Like any big city, use common sense. The tourist areas (Loop, Magnificent Mile, Lincoln Park, Wicker Park) are very safe. Avoid isolated areas late at night. The CTA is generally safe but stay alert on late-night trains.
Packing: Layers, always layers. Chicago weather can swing 30 degrees in a single day. A windbreaker is essential near the lake, even in summer. Comfortable walking shoes are non-negotiable — you will walk more than you expect.