What to do once you land inChicagoFind your bearings
Chicago is a world-class city with Midwest prices. The architecture will stun you, the food scene rivals NYC, and the lakefront gives you 26 miles of free beaches. Locals are genuinely friendly (Midwest nice is real), the neighborhoods each have their own personality, and the L train gets you everywhere. Just don't call it the 'Windy City' around locals.
Neighborhoods
Wicker Park / Bucktown — Indie shops, vinyl stores, cocktail bars, and some of the city's best restaurants packed into a walkable stretch of Milwaukee Avenue
Logan Square — Tree-lined boulevards with craft breweries, acclaimed taco joints, and a younger creative crowd. The gastropub scene is unmatched
Pilsen — Mexican-American neighborhood with incredible murals, authentic taquerias, the National Museum of Mexican Art, and 18th Street's vibrant strip
River North — Gallery district turned nightlife hub with rooftop bars, upscale restaurants, and the city's densest concentration of steakhouses and cocktail lounges
Hyde Park — University of Chicago's neighborhood on the South Side. The Museum of Science and Industry, indie bookshops, and Obama's old stomping ground
Best time to visit
June through September for warm lakefront days, outdoor concerts, and rooftop season. May and October are shoulder months with fewer crowds. Winter (November through March) is brutally cold but hotel prices drop and there's never a wait at restaurants.
Getting around
The L train covers the whole city. Get a Ventra card and ride any line for $2.50. The Brown Line is the scenic route through neighborhoods
Divvy bike-share is perfect for the lakefront trail. $15 for the day with unlimited 3-hour rides
Water taxis run on the Chicago River in summer for $6. Cheaper than Uber and more scenic than the L
Walking the Riverwalk from Michigan Avenue to Chinatown is free and one of the best urban walks in America
Key areas
Wicker ParkLogan SquarePilsenRiver NorthHyde Park
Zero-dollar wins
1
Lincoln Park ZooFree admission year-round (one of the last free zoos in the US). The big cat house and the Nature Boardwalk are highlights
2
Millennium Park and Cloud GateThe Bean (Cloud Gate) is free to visit and more impressive in person. The Pritzker Pavilion hosts free concerts all summer
3
Lakefront Trail18 miles of paved path along Lake Michigan with free beaches, parks, and skyline views. North Avenue Beach is the most popular
4
Chicago RiverwalkWalk the 1.25-mile riverside path through the Loop. Free architecture viewing, public art, and kayak watching from the cafés
5
Pilsen murals walkSelf-guided tour of massive Mexican-American murals on 16th and 18th Streets. Free, colorful, and culturally significant
6
Navy Pier fireworksFree fireworks every Wednesday and Saturday night in summer (Memorial Day through Labor Day). Watch from the pier or the lakefront
7
Art Institute free eveningsFree admission for Illinois residents on select Thursday evenings. One of the world's best art museums, home to A Sunday Afternoon on the Island of La Grande Jatte
Treat yourself
(we think it's worth it)
Alinea$250 to $400
Three-Michelin-star molecular gastronomy from Grant Achatz. The dessert painted on the table is an art installation you eatArchitecture boat tour (CAF)$50 to $65
Chicago Architecture Foundation's river cruise is the single best tour in the city. 90 minutes of stunning buildings narrated by expertsSecond City improv show$30 to $60
Where Tina Fey, Steve Carell, and Bill Murray started. The mainstage show is worth the ticket, but the free improv set after is often betterSignature Room at the 95th$20 to $40
Skip the Willis Tower Skydeck ($30 admission). Have a cocktail at Signature Lounge on the 96th floor of the Hancock for the same view, just buy a drinkThe legendary bites
The dishes this city perfected
Lou Malnati's$15 to $25
The deep dish that locals actually eat. Butter crust, chunky tomato sauce on top, and a blanket of mozzarella. Lincoln Park location is the classicButtercrust deep dish with sausagePortillo's$8 to $14
Chicago's fast-food cathedral. Italian beef (dipped, with hot giardiniera) is the city's true signature food, not deep dishItalian beef, dipped, with hot giardinieraGirl & The Goat$30 to $55
Stephanie Izard's Randolph Street flagship with bold, globally-inspired dishes and a bustling open kitchen. Reserve 3 weeks outGoat empanadasSmyth$185 to $275
Two-Michelin-star tasting menu in a converted Victorian house. Hyper-local ingredients and a quiet elegance that's uniquely ChicagoMulti-course tasting menu (changes seasonally)Superdawg$6 to $12
Drive-in hot dog stand since 1948 with two giant hot dog statues on the roof. Pure Chicago nostalgia with a perfect snap-casing dogSuperdawg with fries in a box (no ketchup allowed)Where locals eat
Where residents actually go
Jim's Original (Maxwell Street)$4 to $7
Polish sausage stand under the highway since 1939. Grilled onions, sport peppers, and mustard on a bun at 2am. Chicago's late-night ritualJohnnie's Beef$8 to $12
Elmwood Park Italian beef counter with no seats and a line out the door. Stand at the counter and lean over your sandwich. Paper towels requiredBirrieria Zaragoza$10 to $16
Weekends-only birria in Archer Heights that locals drive across the city for. The consomé with corn tortillas is transcendentQing Xiang Yuan Dumplings$10 to $18
Chinatown hand-pulled noodles and lamb dumplings in chili oil. The xiao long bao (soup dumplings) rival any in NYCBig Star$12 to $20
Wicker Park taco joint with a whiskey bar, outdoor patio, and tacos that would hold up in Mexico City. The fish taco al pastor is perfectGo off-script
1
Architecture boat tour on the riverThe CAF river cruise is the single best tour in Chicago. 90 minutes on the river learning why these buildings matter. Book the first morning slot for smaller crowds
2
Deep dish: Lou Malnati's vs Pequod'sLou Malnati's is tradition (butter crust, chunky sauce). Pequod's is the caramelized-crust rebel. Try both and pick a side. This is Chicago's real rivalry
3
Blues at Kingston MinesLincoln Park blues club open until 4am with two stages and rotating acts. No cover on weeknights, cheap drinks, and the real Chicago blues experience
4
Sunrise at North Avenue BeachThe beach faces east over Lake Michigan. Arrive at 5:30am in summer for golden light on the skyline and an empty beach. Coffee from the Surf shop opens at 6am
Insider intel + tourist traps
Tips
- ✓Deep dish is a tourist food that locals eat once a year. The real Chicago foods are Italian beef, Chicago-style hot dogs (never ketchup), and jibaritos (plantain sandwiches)
- ✓Winter is serious here. If visiting November through March, pack layers, a good coat, and accept that the wind off the lake adds 10 to 20 degrees of chill
- ✓The 'Loop' refers to the L train loop downtown but also the central business district. Most restaurants in the Loop close early. Nightlife is in the neighborhoods
- ✓Free museum days rotate throughout the year. Check each museum's website for their free admission schedule and plan around it
“Got a free concert at Millennium Park, ate Italian beef twice, biked the lakefront for 15 miles, and caught improv at iO. Chicago might be the most underrated city in America.”
Skip
- ✗Giordano's deep dish: the chain tourist version of deep dish that no local would choose over Lou Malnati's or Pequod's. Skip it
- ✗Willis Tower Skydeck ($30+): long lines and plexiglass ledges. Go to the Signature Lounge on the 96th floor of the Hancock building for free views with a drink purchase
- ✗Navy Pier restaurants: overpriced chains with mediocre food. The fireworks are free but eat before you get there