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FSTNR Week – Chicago Guide

While you're in Chicago for FSTNR Week '26, bring the whole family and take advantage of one of America's greatest cities at its absolute summer peak. Here's your insider's guide to all of it. 

🎶 Old School Chicago

Blues, mob history & legendary nights out
Blues

Buddy Guy's Legends

Owned by Rock & Roll Hall of Famer Buddy Guy — the premier blues club in the world. Live electric blues every single night on South Wabash. Catch a legend in his own house.

buddyguy.com
Blues

Kingston Mines

Chicago's oldest continuously running blues club since 1968. Two stages, two bands, alternating sets all night in Lincoln Park. Open until 4 AM on weekends. The real deal.

kingstonmines.com
Blues

Blue Chicago

Intimate River North blues bar open since 1985. Live electric blues nightly — a block from the Mag Mile, no attitude, just authentic Chicago music every night.

bluechicago.com
Jazz & History

The Green Mill

Open since 1907 — Al Capone's personal favorite, his old booth still reserved. Live jazz every single night. One of the great American bars. Period.

greenmilljazz.com
Mob Tour

Untouchable Gangster Bus Tour

Chicago's original gangster tour for 35+ years. Costumed actor-guides take you on a 2-hour bus tour through Prohibition-era landmarks — Capone, Dillinger, the St. Valentine's Day Massacre site and more.

gangstertour.com
Mob Tour

Chicago Crime Tours

A deeper dive into the underworld — Capone, Frank “The Enforcer” Nitti, H.H. Holmes, Leopold & Loeb. Climate-controlled bus with stops at real historic crime scenes and famous gangster haunts.

chicagocrimetours.com
Steakhouse

Gene & Georgetti

Chicago's oldest steakhouse, open since 1941 under the El tracks in River North. Dark wood, checkered tablecloths, enormous chops, and old-school Italian-American service. Where Chicago power brokers have always eaten.

geneandgeorgetti.com
Old School Ribs

Twin Anchors

An Old Town institution since 1881 — Frank Sinatra's personal favorite Chicago spot. Fall-off-the-bone ribs, vintage bar, a jukebox that still plays Ol' Blue Eyes. Cash only and worth every penny.

twinanchorsribs.com
Perfect Old-School Chicago Night: Gangster Bus Tour in the early evening → dinner at Gene & Georgetti → live blues at Buddy Guy’s Legends or a nightcap at The Green Mill. That’s a Chicago evening nobody forgets.

★ Iconic Chicago Experiences

The bucket-list moments that define this city
Must Do

Architecture River Cruise

Voted #1 boat tour in the US by USA Today. A 90-minute narrated cruise past 50+ iconic skyscrapers. The single most Chicago thing you can do — book early, it sells out weeks ahead.

architecture.org
Must Do

Wrigley Field — Cubs Game

An American classic. See a game at one of the oldest ballparks in the country — ivy walls, rooftop bleachers, the whole scene. Take the backstage tour if no game is scheduled.

mlb.com/cubs
Must Do

Willis Tower Skydeck

Step out onto The Ledge — glass-floored balconies on the 103rd floor, 1,353 feet above Chicago. The highest observation deck in the US. Views of four states on a clear day.

theskydeck.com
Must Do

Millennium Park & The Bean

Cloud Gate, Crown Fountain, free outdoor concerts — all completely free. The Bean is the must-photograph Chicago moment. Walk the lakefront trail to Navy Pier from here.

chicago.gov
Views

360 Chicago Observation Deck

94th floor of the historic John Hancock Center on the Mag Mile. 360° skyline and lake views. Try TILT — the tilting window experience over Michigan Avenue.

360chicago.com
On the Water

Kayaking the Chicago River

Paddle right through downtown between the skyscrapers — one of the most unique urban experiences in America. Guided tours and rentals available from the Riverwalk. No experience needed.

chicagoriverwalk.us
Beach

Oak Street Beach

A real beach — white sand, clear water, skyline looming behind you. Chicago's most iconic stretch of Lake Michigan shoreline, steps from the Magnificent Mile. Free, stunning, and very Chicago.

chicago.gov/beaches
New in 2026

The Hand & The Eye

Brand new in 2026 — the world's largest magic venue inside the historic McCormick Mansion in the Gold Coast. Multiple floors of immersive magic performances, bars, and dining. Truly one-of-a-kind.

choosechicago.com
Pro Tip: Book the architecture river cruise and Willis Tower Skydeck in advance — both sell out in summer.  •  Aug 30 (Saturday) is Navy Pier fireworks night at 10:15 PM — a spectacular first night!

✦ Indulge & Unwind

Luxury, relaxation & world-class shopping
Spa

Chuan Spa at The Langham

Chicago's most acclaimed luxury spa — heated stone loungers, herbal saunas, steam rooms, and world-class massage. A full-day retreat in one of the city's finest hotels. Book in advance.

langhamhotels.com
Rooftop Dining

Cindy's Rooftop

Rooftop dining atop the Chicago Athletic Association Hotel — panoramic views of Millennium Park and Lake Michigan. Perfect for a long, celebratory lunch with cocktails.

cindysrooftop.com
Shopping

Magnificent Mile

Over a mile of flagship stores, boutiques, and designer brands along Michigan Ave — Nordstrom, Bloomingdale’s, luxury brands, and one-of-a-kind Chicago shops. World-class retail in a world-class setting.

themagnificentmile.com
Fine Dining

Shanghai Terrace at The Peninsula

Hidden-garden rooftop terrace on the Mag Mile serving Cantonese delicacies and classic dim sum. One of Chicago’s most intimate and elegant dining experiences. Reserve ahead.

peninsula.com
Rooftop Dining

LH Rooftop at LondonHouse

22nd floor rooftop on the Chicago River — jazz-age cocktails, American fare, and one of the absolute best sunset views in the city. Reserve well in advance.

londonhousechicago.com
Fine Dining

Monteverde Restaurant

James Beard Award-winning Chef Sarah Grueneberg’s beloved West Loop pasta restaurant. One of the best Italian spots in America — house-made pastas, serious wine list. Reserve well ahead.

monteverdechicago.com

🎨 Arts, Culture & Museums

World-class institutions steps from downtown
Art

Art Institute of Chicago

One of the world's great art museums — Monet, Van Gogh, Picasso, Seurat’s Sunday on La Grande Jatte. Currently showing a major de Kooning drawings exhibition through September 20. Closed Tuesdays.

artic.edu
Science

Museum of Science & Industry

The largest science museum in the Western Hemisphere — a real WWII submarine, a coal mine ride, and the famous whispering gallery. Kids and adults equally captivated.

msichicago.org
Natural History

The Field Museum

Nearly 40 million artifacts and specimens, including SUE — the most complete T. rex ever discovered. The Pokémon Fossil Museum exhibit opens May 2026. On the lakefront Museum Campus.

fieldmuseum.org
History

Obama Presidential Center

Opening spring 2026 — the former president lived on Chicago’s South Side for two decades. Set in historic Jackson Park, featuring exhibits, performances, and community events. A landmark opening.

obama.org

◆ Kids & Family Adventures

Crowd-pleasers that delight every age
Kids Love It

Shedd Aquarium

World-class aquarium on the lakefront — beluga whales, dolphin shows, Amazon rainforest exhibit, and starfish touch tanks. Plan 3+ hours. One of the top aquariums in the world.

sheddaquarium.org
Kids Love It

Chicago Children’s Museum

Right on Navy Pier — three floors of hands-on exhibits where kids can be firefighters, use construction equipment, and splash in water areas. Ages 1–10.

chicagochildrensmuseum.org
Family

Navy Pier

Centennial Ferris wheel, restaurants, boat rides, and gorgeous Lake Michigan views. Saturday night fireworks at 10:15 PM — Aug 30 is a Saturday. Don’t miss it.

navypier.org
Family

Maggie Daley Park

A free 20-acre adventure playground next to Millennium Park — climbing walls, mini golf, and themed play areas that wow kids and parents alike. Completely free.

maggiedaleypark.com
Family

Lincoln Park Zoo

One of the last free major zoos in America — lions, gorillas, polar bears, and more in the heart of Lincoln Park, steps from the lakefront. Free admission, all summer long.

lpzoo.org
Family

Chicago Riverwalk

A mile-long pedestrian path along the main branch of the Chicago River — restaurants, bars, boat tours, kayak rentals, and stunning architecture views. The city’s outdoor living room.

chicagoriverwalk.us
Save big: Chicago CityPASS bundles Shedd Aquarium + Architecture River Tour + 3 more top attractions at up to 50% off. Perfect for families seeing Chicago for the first time. → citypass.com/chicago

🍕 Chicago Food Classics

Dishes you can only get right here
Must Eat

Lou Malnati’s Deep Dish Pizza

The gold standard of Chicago deep dish since 1971. Signature butter crust, Italian sausage, and extra cheese. Call ahead — it takes 45 minutes to bake. Worth every minute.

loumalnatis.com
Must Eat

Portillo’s Chicago-Style Hot Dog

Vienna Beef frank on a poppy seed bun — yellow mustard, relish, onion, tomato, pickle, sport peppers, celery salt. Never ketchup. A Chicago religion since 1963.

portillos.com
Must Eat

Gene & Georgetti

Chicago’s oldest steakhouse, open since 1941 under the El tracks in River North. Dark wood, checkered tablecloths, enormous chops, and old-school Italian-American service.

geneandgeorgetti.com
Fine Dining

Alinea

Three Michelin stars — one of the best restaurants in the world, right here in Lincoln Park. Chef Grant Achatz’s avant-garde tasting menu is a full theatrical experience. Reserve months out.

alinearestaurant.com
Must Eat

Pequod’s Pizza

Chicago’s cult-favorite deep dish — famous for its caramelized cheese crust that forms a dark, crispy ring around every pie. A local’s choice over the tourist spots. Worth the wait.

pequodspizza.com
Italian Beef

Al’s Beef — Italian Beef Sandwich

The Chicago Italian beef sandwich — thinly sliced seasoned beef, soaked in au jus, on a chewy roll, topped with giardiniera or sweet peppers. Order it “dipped.” As Chicago as it gets.

alsbeef.com
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