Plan & Navigate
Quick Facts & Essentials
💰
Money & Costs
Currency: US Dollar (USD, $). 1 USD ≈ 0.92 EUR [ASSUMPTION — check current rate]
Card-dominant city. Tap-to-pay accepted almost everywhere including CTA turnstiles, taxis, food trucks. Carry $20-40 cash for tipping, dive bars, and small vendors. ATMs everywhere — use bank ATMs (Chase, BMO) to avoid $5+ fees from bodega machines. Tipping: 18-22% restaurants, $1-2/drink at bars, $2-5/bag for hotel porters, 15-20% for rideshare and taxis.
Budget: Budget: $90-130/day (hostel, deep-dish slice, CTA day pass). Mid-range: $200-320/day (boutique hotel, sit-down dinners, a few cocktails, museum entry). Luxury: $500+/day (Loop or Gold Coast hotel, Alinea-tier dining, private architecture tour).
🗣️
Language
Official: English is the working language everywhere. Spanish is widely spoken in Pilsen, Little Village, Humboldt Park, and most service industries. Polish, Mandarin, and Cantonese common in specific neighborhoods (Avondale, Chinatown).
Zero barrier for English speakers. Staff in tourist zones often speak multiple languages. Menus and signage in English citywide.
Useful: The Loop (Downtown business district inside the elevated train circle), The L (Elevated/subway train system (CTA rail)), Pop (Soda or soft drink), Gym shoes (Sneakers/trainers), LSD (Lake Shore Drive — the lakefront highway, not the drug)
🚗
Getting Around
Chicago has one of the best transit systems in the US. The L plus buses will get you 90% of where you want to go for cheap. Skip rental cars unless you're heading to the suburbs — parking downtown runs $40-70/day and traffic on the Kennedy is brutal. Walk the Loop and River North; transit everything else.
CTA L Train: Eight color-coded lines. Blue Line connects O'Hare to downtown in ~45 min. Red Line runs 24/7 north-south through the Loop. Use Ventra app or tap a contactless card directly at turnstiles. — $2.50/ride, $5 unlimited day pass, $20 7-day pass. O'Hare entry $5.
CTA Bus: Fills gaps the L doesn't reach — especially east-west routes and the lakefront. #146 and #151 are scenic along Michigan Ave and Lake Shore Drive. — $2.25/ride, free transfers within 2 hours
Divvy Bikes: Citywide bike share with protected lakefront trail (18 miles, flat, gorgeous). Best way to cover the lakefront from Hyde Park to Lincoln Park. — $1 unlock + $0.18/min, or $18 day pass for unlimited 45-min rides
Rideshare (Uber/Lyft): Reliable everywhere. Surge pricing hits hard during Cubs/Bears games and after 2am bar close. Downtown congestion fee adds $1.75-3. — $10-20 most in-city trips, $40-55 to/from O'Hare
Metra: Commuter rail to suburbs and Indiana Dunes. Useful for day trips, not city sightseeing. — $4-10 depending on zones
⚠️ Safety Note: Chicago's reputation is worse than the reality for tourists, but be specific about geography. The Loop, River North, Gold Coast, Lincoln Park, Wicker Park, Pilsen, and Hyde Park (around U of Chicago) are fine day and night with normal city awareness. Avoid wandering West Garfield Park, Englewood, and parts of the far South and West Sides — not tourist areas anyway. Lower Wacker and the Pedway feel sketchy late at night; take the street. Phone snatching on the Red and Blue Lines has spiked — don't scroll with your phone in hand near closing doors. Lakefront Trail is safe and busy until dusk; thins out fast after dark north of Oak Street Beach. Summer holiday weekends (July 4th, Memorial Day) see occasional flash crowds downtown — police shut down Millennium Park early some nights.
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When to Go
Dec–Feb
Weather
Highs -1 to 2°C (30–35°F), lows -8 to -5°C (18–23°F). Snow 25–30cm/month. Wind chill regularly drives feel-temp to -20°C/-4°F
Crowds
Low
Best For
Hotel deals, museum days (Art Institute, Field), holiday markets at Daley Plaza, ice skating at Maggie Daley and Millennium Park, blue hour cityscapes from Adams/Wabash with snow on the L tracks
Watch Out
Brutal lakefront wind — the 'Hawk' is real. Some patios and architecture boat tours shut down. Days are short (sunset ~4:30pm in Dec). Sidewalks ice up; bring traction-friendly boots
Bottom Line: Late September through mid-October is the clear winner: stable 18–22°C days, dry air, foliage building toward peak, and long enough light to walk neighborhoods from breakfast through blue hour. Mid-May into early June is a strong second window — patios reopen, festivals start, and crowds haven't yet hit Lolla-level density.
What to Experience
★★★★★ Cloud Gate (The Bean) at Millennium Park
Yes, it's overhyped and mobbed — but skip it and you'll regret it. The reflections of the skyline genuinely deliver, and it's free. Just don't expect a quiet moment with it.
🕐 Best Time: Sunrise (before 7am) for empty plaza, or blue hour for skyline lights in the reflection
💡 Insider Tip: Arrive before 7am for clean reflections without crowds in frame. Shoot from underneath looking up for the kaleidoscope effect everyone misses.
💰 Fees: Free
🎟️ Booking: None
★★★★★ Art Institute of Chicago
World-class collection — Hopper's Nighthawks, Seurat's La Grande Jatte, a serious Impressionist wing. Worth a half day minimum. The modern wing is underrated compared to the headliners.
🕐 Best Time: Weekday mornings right at 11am open; Thursdays stay open until 8pm and feel calmer after 5pm
💡 Insider Tip: Enter through the Modern Wing on Monroe Street to skip the Michigan Avenue line. Free for Illinois residents on select Thursdays [ASSUMPTION — verify current schedule].
💰 Fees: $32 adults, $26 seniors/students [ASSUMPTION — check current pricing]
🎟️ Booking: Book online to skip ticket line
★★★★★ Chicago Riverwalk + Architecture Boat Tour
The architecture cruise is the rare tourist activity that locals also recommend. Chicago invented the skyscraper and this is the only way to actually see them. The Riverwalk itself is a great free stroll if you skip the boat.
🕐 Best Time: Late afternoon departures (around 4–5pm) catch golden hour on the buildings
💡 Insider Tip: Book Chicago Architecture Center's tour, not the cheaper knockoffs — their docents are trained architects. Sit on the upper deck, starboard side heading out for best light on east-facing buildings.
💰 Fees: Riverwalk free; CAC boat tour around $55
🎟️ Booking: Book 2–3 days ahead in summer
★★★★☆ 360 Chicago (Hancock Observatory)
Better than Skydeck for one reason: you can see the Hancock itself from Skydeck, but from 360 you look down the Magnificent Mile and along the lake. The Tilt add-on is more novelty than essential — fun once if you're already there, but don't make it the reason you go. The Signature Lounge one floor up gives you the same view for the price of a drink.
🕐 Best Time: Arrive 45 min before sunset to shoot daylight, sunset, and blue hour from one spot
💡 Insider Tip: Skip the $30 ticket and go to the Signature Lounge on floor 96 instead — buy a $18 cocktail, get the same view, and sit down.
💰 Fees: $30 observatory; or price of one drink at Signature Lounge
🎟️ Booking: None needed off-season; book ahead summer weekends
★★★★☆ Garfield Park Conservatory
Free Victorian-era greenhouse on the West Side that most tourists never hear about. Six rooms of palms, ferns, and desert plants — phenomenal rainy-day shoot location with diffused natural light. Genuinely one of the best free things in the city.
🕐 Best Time: Weekday mornings, overcast days are best — direct sun creates harsh contrast through the glass
💡 Insider Tip: Fern Room is the photo shot — the prehistoric vibe with the lagoon. Bring a lens cloth; humidity will fog your gear walking in.
💰 Fees: Free (suggested donation)
🎟️ Booking: Free timed-entry passes online during busy periods
★★★★☆ Pilsen Neighborhood + 16th Street Murals
Mexican-American neighborhood with the most concentrated street art in the city, plus the National Museum of Mexican Art (free, excellent). The 16th Street train embankment murals run for blocks. Skip the Loop for an afternoon and come here.
🕐 Best Time: Saturday afternoons for street life; murals shoot best with overcast or late afternoon side light
💡 Insider Tip: Start at the museum, walk south to 18th Street for taquerias (Carnitas Uruapan is the move), then hit the 16th Street murals on your way back. Pink Line to 18th Street stop.
💰 Fees: Free
🎟️ Booking: None
★★★☆☆ Promontory Point
Limestone peninsula jutting into Lake Michigan in Hyde Park with the single best skyline view in the city — and almost no tourists. The skyline sits across the water like a postcard. Locals come here to swim off the rocks in summer.
🕐 Best Time: Sunrise for golden light hitting the buildings; blue hour also strong
💡 Insider Tip: Sunrise here is the shot — skyline lights up gold while you have the place to yourself. Bring a wide lens; you're far enough away that the whole skyline fits.
💰 Fees: Free
🎟️ Booking: None
★★★☆☆ Wrigley Field
Even if you don't care about baseball, a Cubs game at Wrigley is a legitimate cultural experience — ivy walls, hand-turned scoreboard, the whole thing. Tours are fine but the game-day energy is the point. Navy Pier is the more famous attraction and frankly skippable; come here instead.
🕐 Best Time: Day games (1:20pm starts) April–September; weekday games are cheaper and less packed
💡 Insider Tip: Sit in the bleachers for the real Wrigley experience, not behind home plate. Day games are the tradition. Arrive early and walk Sheffield and Waveland for the rooftop view setup.
💰 Fees: Tickets from $20 upper deck to $200+; tours around $30
🎟️ Booking: Book ahead for weekend games and Cardinals/Yankees series
Scenic Routes
Lakefront Trail
📏 29km / 2-3hr ride
- Continuous skyline views from multiple angles as you move south
- Passes Navy Pier, Museum Campus, and Promontory Point
- Best skyline reflection shots from 31st Street Beach at golden hour
Chicago Riverwalk
📏 2km / 45min walk
- Bridge-level views of the Wrigley Building, Tribune Tower, and Marina City
- Architecture boat tours launch from here if you want the water-level perspective
- Blue hour shots from under the Michigan Ave bridge are unbeatable
606 Trail (Bloomingdale Trail)
📏 4.3km / 1hr walk
- Elevated former rail line through Logan Square, Humboldt Park, and Wicker Park
- Street art and neighborhood rooftop views you cannot get from the ground
- Quieter alternative to the Lakefront Trail with local feel
Lake Shore Drive (DuSable)
📏 25km / 30-45min drive
- The classic skyline reveal coming southbound past Oak Street Beach
- Lake Michigan on one side, high-rises on the other for most of the drive
- Pull off at North Ave Beach or Montrose Point for skyline shots
Loop Architecture Walk
📏 3km / 1.5hr walk
- Rookery Building lobby (Frank Lloyd Wright redesign) is free to enter on weekdays
- Marquette Building, Monadnock, and the Chicago Board of Trade in one loop
- Look up constantly, but also shoot reflections in The Bean at Millennium Park to close the walk
Northerly Island & Museum Campus Loop
📏 3.5km / 1hr walk
- Best frontal skyline view in the city from the Adler Planetarium steps
- Northerly Island has prairie grasses and a quieter shoreline path
- Sunset here lights up the entire downtown face [ASSUMPTION] best Sept-Nov when sun aligns west of skyline
Street Art in Chicago
Chicago's street art scene is one of the most legitimate in the US, anchored by the Wabash Arts Corridor in the South Loop and the deep mural traditions of Pilsen and Logan Square. The city embraces large-scale commissioned work alongside scrappy paste-ups and stickers, with rotating walls keeping the scene fresh year to year. Pilsen's Mexican-American muralism dates back to the 1970s and is genuinely historic, not Instagram-bait.
★★★★★ Stop 1
An open-air gallery curated by Columbia College along S Wabash. Massive building-side pieces by international artists rotate every few years. Easiest concentrated mural walk in the city.
🎨 Artists: Hebru Brantley, Shepard Fairey, INTI, Pose, Don't Fret, Ever Siempre
🕐 Best time: 10am–1pm for even light on east-facing walls
★★★★★ Stop 2
A long railroad embankment turned continuous mural wall. Dense, layered, and genuinely community-rooted. The strongest single corridor of street art in Chicago for photographers who want texture and scale.
🎨 Artists: Sentrock, Robert Valadez, Pablo Serrano, plus rotating local Pilsen artists
🕐 Best time: Late afternoon golden hour; walls face south
★★★★☆ Stop 3
The commercial spine of Pilsen with murals tucked between taquerias, panaderías, and galleries. Stop at Thalia Hall area and the National Museum of Mexican Art (free) to contextualize what you're shooting.
🎨 Artists: Hector Duarte (Gulliver in Wonderland nearby), Jeff Zimmermann, Salvador Jiménez-Flores
🕐 Best time: Morning for east-facing facades, late afternoon for west
★★★★☆ Stop 4
Spread out but rewarding. Murals along Milwaukee Ave and side streets, with strong work around the Logan Theatre and Hairpin Arts Center. Pair with coffee and record shops if you're making a half-day of it.
🎨 Artists: Sam Kirk, Sandra Antongiorgi, Rahmaan Statik, JC Rivera (The Bear Champ)
🕐 Best time: Afternoon; many walls face west or south
★★★☆☆ Stop 5
Fulton Market's meatpacking-turned-tech district has commissioned facade pieces, but it leans corporate and polished. Worth a pass-through if you're already there for food, otherwise skippable compared to Pilsen. [ASSUMPTION] Specific walls rotate frequently with new development.
🎨 Artists: Various commissioned muralists; check Vertical Gallery for current map
🕐 Best time: Midday; tall buildings cast long shadows otherwise
💎 Hidden Gems
Hector Duarte's Gulliver in Wonderland on the side of his home studio at 1900 W Cullerton St in Pilsen is one of the best single murals in the country and most tourists never make it that far south. The alley behind Reckless Records in Wicker Park has rotating paste-ups and stickers that change monthly. The Pilsen Mural Tour offered by local artists (book through the Chicago Urban Art Society) gets you context you'll never get walking solo.
📋 Practical Notes
Pilsen is a working Mexican-American neighborhood, not a backdrop. Don't shoot people without asking, don't block storefronts, and consider buying lunch at Carnitas Uruapan or Don Pedro before you leave. Walls rotate every 1–3 years on commissioned corridors, faster on unsanctioned spots. Wabash and Pilsen are both safe in daytime; use normal city awareness after dark. Vertical Gallery (Wicker Park) maintains an informal map of current major works and runs occasional guided tours.
Eat & Drink
Chicago's food scene is built on immigrant traditions and unapologetic portion sizes. Deep-dish pizza, Italian beef, and Chicago-style hot dogs get the headlines, but the city's real depth lives in its neighborhood spots: Polish delis in Avondale, taquerias in Pilsen, Vietnamese pho counters in Uptown, and steakhouses that still mean something. The fine-dining tier punches above its weight too, with Alinea-era alumni scattered across Logan Square and the West Loop. What makes it distinctive is the lack of pretension. Even the tasting-menu crowd here keeps a Midwestern friendliness, and you'll pay 20-30% less than equivalent rooms in NYC or LA. Skip the deep-dish tourist traps on Michigan Ave and eat where locals actually go.
Coffee, Cafés & Bakeries
Intelligentsia Coffee
Specialty: Single-origin pours, Black Cat espresso, Chicago roasting pioneer
📍 Multiple; the Millennium Park location at 53 E Randolph is most central
Mornings before 9am are calm. Cash-equivalent prices, fast wifi at the Logan Square cafe.
Sawada Coffee
Specialty: Military latte (matcha-espresso-cocoa), Japanese precision
📍 West Loop, 112 N Green St
Shares space with Green Street Smoked Meats. Photogenic counter, busy 10am-2pm weekends.
Ipsento 606
Specialty: Ipsento latte with cayenne and coconut, neighborhood vibe
📍 Bucktown, 1813 N Milwaukee Ave
Right on the 606 trail. Good for a post-walk stop.
Sparrow Coffee
Specialty: Minimalist Scandi-style space, careful filter coffee
📍 Gold Coast, 12 E Pearson St
Quiet for laptop work weekday afternoons. Limited seating.
Lost Larson
Specialty: Cardamom buns, rye loaves, Scandinavian pastries
📍 Andersonville, 5318 N Clark St
Sells out of cardamom buns by 11am Saturdays. Andersonville's Swedish heritage made real.
Bombobar
Specialty: Filled bomboloni, hot chocolate shots in chocolate-rimmed cones
📍 West Loop, 832 W Randolph St
Lines on weekends but moves fast. Highly photogenic.
Middle Brow Bungalow
Specialty: Naturally-leavened breads, wood-fired pizza, beer too
📍 Logan Square, 2840 W Armitage Ave
Bakery counter mornings, restaurant evenings. Not on most tourist radars.
Other
★★★★★ Lou Malnati's
Specialty: Deep-dish pizza with butter crust and sausage patty
Order ahead online, deep-dish takes 45 min to bake. The Lincolnwood location is the closest to the founding spirit.
★★★★★ Alinea
Specialty: Avant-garde tasting menu, edible balloons, tableside dessert paintings
Tickets released monthly, sell out within hours. Expect $300-500+ per person. Worth it once.
★★★★☆ Al's Beef
Specialty: Italian beef sandwich, dipped, with hot giardiniera
Order it 'dipped wet' and eat over the counter, leaning forward. Cash-friendly, fast line.
★★★★☆ Girl & the Goat
Specialty: Wood-fired small plates, goat empanadas, pig face
Stephanie Izard's flagship. Book 4 weeks out or grab bar seats at 5pm walk-in.
★★★☆☆ Kasama
Specialty: Filipino breakfast by day, Michelin tasting menu by night
Walk in for the breakfast longanisa plate. Tasting menu requires booking months ahead.
Althea
Specialty: Plant-forward Mediterranean tasting menu, fully vegan options
[ASSUMPTION] Reservations recommended on weekends. Higher-end pricing.
Handlebar
Specialty: Vegetarian comfort food, BBQ tofu sandwich, beer garden
Patio is great in summer. Casual, mostly veg menu with vegan marks clearly noted.
Amitabul
Specialty: Korean Buddhist vegan, healing noodle soups, no garlic or onion
Far north and worth the trek. Cash only [ASSUMPTION], small dining room.
Budget Eating Strategy
Hit Italian beef and hot dog joints (Al's, Portillo's, Jim's Original) for under $10 lunches that are also the iconic experience.
Many top restaurants offer bar seating walk-in only, reservations needed only for tables. Show up at 5pm sharp at Girl & the Goat, Au Cheval, or Avec.
The Maxwell Street Market on Sundays in Pilsen has $3-5 huaraches, tamales, and tacos that beat most sit-down Mexican spots in the city.
See Through the Lens
Cloud Gate (The Bean)
Best: Sunrise 5:30–6:30am summer, 7:00am winter. You get clean reflections without crowds. By 9am it's a sea of selfie sticks.
Chicago Riverwalk at LaSalle Street Bridge
Best: Blue hour, roughly 30 minutes after sunset. Building lights pop while sky retains color. Also stunning during summer bridge lifts (Saturdays).
Adler Planetarium Skyline View
Best: Blue hour after sunset for lit skyline against deep blue sky. Sunrise also works with sun behind the buildings (silhouette mood).
Chicago Theatre Marquee
Best: Night, after 7pm when sign is fully lit and street has light trails. Tuesday–Thursday for thinner crowds.
Damen Blue Line Station, Wicker Park
Best: Golden hour for warm light on brick, or rainy night for neon reflections in puddles. Rush hour adds train action.
Promontory Point
Best: Sunrise — sun rises over the lake to your left, lighting skyscrapers in warm orange. Way fewer photographers than Adler.
360 Chicago (formerly Hancock) Observation Deck
Best: Arrive 90 minutes before sunset, shoot day-to-blue-hour transition through the windows.
Pilsen Murals on 16th Street
Best: Overcast midday is actually best — even light, saturated colors, no harsh shadows on murals. Or golden hour for warm side-light.
Gear: A 24-70mm covers 80% of Chicago. Add a 16-35mm for tight Riverwalk architecture and a 70-200mm for compressed skyline shots from Adler or Promontory. A small travel tripod (Peak Design or similar) flies under the radar where full-size tripods get hassled. Bring a rubber lens hood for any observation deck — it's a $15 item that saves the shot. Lake Michigan wind is no joke; weight your tripod with your camera bag. Seasonal light: Winter (Dec–Feb) gives you 4:30pm blue hour, meaning you can shoot golden-to-blue without staying out late, but expect brutal wind off the lake. Summer means 8:30pm sunsets and lush green parks but heavy crowds at Cloud Gate. Spring and fall are the sweet spots — soft light, dramatic clouds, manageable tourists. Editing-wise, Chicago's signature steel-and-glass skyline benefits from cool-shadow/warm-highlight splits in Lightroom; lift the blues in shadows around -10 to -15 saturation to avoid that overly-teal Instagram look. Pilsen and the L stations are the opposite — push warmth and grain for character.
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Plan Your Days
How Long Do You Need?
Chicago rewards walkers and photographers like few American cities — if you only have one day, anchor it at Millennium Park, walk the Riverwalk west, and end on the 360 Chicago observation deck at sunset for the city's best skyline-meets-lake view.
⚙️ Hidden Gems and Off the Beaten Path
Start at the Rookery Building lobby (LaSalle St) to see the Frank Lloyd Wright light court. Walk east to the Chicago Cultural Center (free, check the Tiffany dome). Cross Millennium Park, passing through Lurie Garden at the south end. Cross the BP Pedestrian Bridge to Maggie Daley Park. Walk south through Grant Park to the Field Museum area, then take the Orange or Green Line to Halsted and walk to Palmisano Park in Bridgeport for the skyline view from the quarry hill. Total: about 3.5 hours with stops. Best done starting mid-morning on a weekday.
- Palmisano Park - skyline panorama framed by prairie grasses at golden hour
- Osaka Japanese Garden - reflections, bridges, autumn color in Jackson Park
- Rookery Building Lobby - Frank Lloyd Wright light court, ironwork staircase
- Riverwalk East Extension at sunrise - river-lake confluence with towers
- Wolf Point at sunrise - three-river junction and 333 W Wacker reflections
- Garfield Park Conservatory Palm Room - tropical cathedral with steam and glass
- Pilsen murals - enormous, vibrant, and deeply photogenic street art
- Promontory Point - sunset skyline from Hyde Park lakefront rocks
- Lurie Garden - Piet Oudolf perennials with skyline backdrop
- Graceland Cemetery - Eternal Silence statue and Getty Tomb by Sullivan
- Pilsen - murals, Mexican food, the National Museum of Mexican Art, strong creative community
- Bridgeport - Palmisano Park, Bridgeport Art Center, old-school Chinese and Lithuanian bakeries, working-class texture
- Andersonville - Swedish heritage, indie bookshops, queer-friendly, outstanding food strip on Clark St
- Hyde Park - University of Chicago, Promontory Point, Osaka Garden, Frank Lloyd Wright's Robie House
- Logan Square - beautiful boulevards, craft cocktail bars, the Logan Theatre, diverse food scene
- Humboldt Park - Paseo Boricua, Prairie-style boathouse, jibaritos, Puerto Rican cultural heart
- Garfield Park Conservatory - free, better than Lincoln Park Conservatory, and on the Green Line
- National Museum of Mexican Art - permanently free, world-class collection
- Palmisano Park - free skyline views that rival any paid observation deck
- Chicago Cultural Center - free, has the world's largest Tiffany dome, rotating exhibitions
- Rookery Building Lobby - free, walk-in, Frank Lloyd Wright masterwork
- Pilsen mural walk - free outdoor gallery spanning blocks
- The Pedway - free underground city exploration
- Lurie Garden - free Piet Oudolf garden in Millennium Park
- Alfred Caldwell Lily Pool - free Prairie-style landscape gem
- Promontory Point - free sunset spot beloved by locals
- Garfield Park Conservatory - warm, lush, and transporting on a gray day
- The Pedway - explore 40 blocks of underground Chicago without getting wet
- National Museum of Mexican Art - immersive, free, and perfect for a rainy afternoon
- Intuit: The Center for Intuitive and Outsider Art - small, fascinating, and dry
- Myopic Books - lose yourself in three floors of used books in Wicker Park
- The Rookery Building Lobby - quick, free, jaw-dropping architecture stop
- Chicago Athletic Association Game Room - play bocce and shuffleboard in a Gothic Revival palace
- Chicago Cultural Center - free exhibitions, concerts, and the Tiffany dome
Navy Pier - unless you have kids who want rides, it is a generic tourist pier with chain food. Skip it.Giordano's or Lou Malnati's in the Loop - the suburban and neighborhood locations are the same food without the 90-minute tourist wait. Go to the Lincoln Park or Lincoln Square locations instead.Skydeck Ledge at Willis Tower - the glass boxes are fun for Instagram but the line is brutal and the views from the Signature Lounge (Hancock, 96th floor) are better and include the Willis Tower itself in the skyline. Save your time.Magnificent Mile shopping - it is the same stores you have at home. Walk Milwaukee Ave through Wicker Park or Clark St through Andersonville for actual Chicago shopping.The Bean (Cloud Gate) at midday - it is worth seeing, but go at sunrise or twilight when the reflections are dramatic and the crowds are gone. At noon it is a selfie scrum.