Chicago
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Chicago is the American city that does everything properly — architecture, food, public transit, lakefront — without the self-consciousness of New York or the sprawl of LA.
Chicago is the American city that architecture writers use to calibrate everything else. The city was leveled by the Great Fire of 1871 and rebuilt by a generation of architects — Sullivan, Burnham, Adler — who invented the steel-frame skyscraper while the rest of the world was still building in stone. You can trace the evolution of modern architecture walking a single downtown block: Romanesque before the fire, Beaux-Arts in the optimistic 1890s, the Gothic Revival Tribune Tower, the Miesian glass boxes of the 1950s, and the postmodern Humana-style towers of the 1980s, ending with the Santiago Calatrava curves at Soldier Field. The Chicago Architecture Foundation river cruise is one of the best two hours in American urban tourism, and it costs $47.
The food is genuinely serious, in a way that is not always credited outside the city. Chicago has a deep-dish pizza tradition that's worth trying exactly once to understand the genre (Lou Malnati's is the reference), but the city's contemporary food landscape is built on something more interesting. The farm-to-table movement ran through Charlie Trotter's kitchen in the 1980s and filtered through a generation of chefs who trained there. Alinea by Grant Achatz made the Chicago tasting-menu circuit globally significant. The Thai Town on Argyle, the Mexican neighborhoods of Pilsen and Little Village, the Vietnamese community on Argyle, and the dim sum parlors in Chinatown mean you can eat at the highest level of global cooking without leaving the city limits.
The lakefront is Chicago's wildcard advantage over every other landlocked American city. Lake Michigan is not an ocean, but it does a convincing impression of one — 118 miles long, cold (50–65°F in summer), and backed by a continuous 18-mile parks ribbon running the length of the city. The Riverwalk downtown, the beaches at Montrose and North Avenue (free, genuinely swimmable in August), and the Lakefront Trail (18 miles of running and cycling path) give Chicago an outdoor infrastructure that San Francisco would be jealous of.
The neighborhoods outside the Loop contain most of the city's actual daily texture. Wicker Park and Bucktown have the most concentrated restaurant and bar scene per square mile. Logan Square is where the younger chefs and natural-wine bars went when Wicker Park rents climbed. Pilsen is the Mexican-American arts and food district on the Near South Side — murals, bakeries, and Nuevo León taqueria on an average block. Hyde Park has the Museum of Science and Industry and the University of Chicago campus. Each of these is 20–40 minutes from downtown on the L train.
The practical bits.
- Best time
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May – June · September – OctoberMay through June is the sweet spot: the city exhales after winter, the lakefront blooms, and temperatures are warm without summer heat. September through October is equally good — Golden Hour light in the 30th-floor bars, the lakefront without humidity, and the architecture tour boats still running. July and August are legitimately wonderful (the festivals, the beach, the outdoor dining) but hot and crowded. November through March is cold (−10°C is possible), grey, and genuinely challenging — Chicago winters have earned their reputation.
- How long
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4 nights recommendedThree nights: the Architecture Tour, Millennium Park, one neighborhood (Wicker Park or Pilsen), and a deep-dish. Four nights adds the Art Institute, a lakefront bike ride, Logan Square, and a proper cocktail bar evening. Seven or more is for people who want to live in Chicago for a week.
- Budget
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$200 / day typicalChicago is more affordable than New York or San Francisco for comparable quality. Budget travelers in Logan Square or Wicker Park can manage on $85–95/day including a hostel. Mid-range — decent hotel in the Loop or River North, sit-down restaurants, attractions — runs $190–220/day. The high-end tasting menus (Alinea, Smyth, Ever) cost $200–350 per person before wine.
- Getting around
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CTA L train + walkingChicago has one of the best urban rail networks in the US. The L (elevated train) runs 8 lines covering the Loop and most neighborhoods of interest ($2.50 per ride, $10 for a 1-day pass). The Red Line (north-south) and Blue Line (O'Hare) are the most useful. Walking is excellent in the Loop, River North, and Millennium Park areas. Lyft and Uber cover the gaps. Divvy bike share ($3.30/30 min) handles the lakefront and the shorter between-neighborhood moves. You don't need a rental car in Chicago.
- Currency
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US Dollar (USD) · universalCards universally accepted. Apple Pay and contactless standard. Cash useful for some taco trucks in Pilsen, parking meters, and small cash-only spots that still exist in neighborhood restaurants. CTA Ventra card (reloadable transit card) is cleaner than tapping individual rides.
- Language
- English. Spanish widely spoken in Pilsen, Little Village, and Humboldt Park. Polish in the Avondale neighborhood. Strong international communities throughout.
- Visa
- US citizens: no visa. International visitors: ESTA for waiver-eligible nationalities. Full tourist visa for others. Chicago's O'Hare is a major international hub with customs and immigration facilities.
- Safety
- Chicago has a significant gun violence problem in specific South and West Side neighborhoods that is genuinely serious — but it's geographically concentrated in areas tourists don't visit. The Loop, River North, Lincoln Park, Wicker Park, Logan Square, and the lakefront are safe by any urban standard. Pilsen (the tourist-friendly Mexican neighborhood) is safe during the day and early evening. Check neighborhood-specific crime maps; the concentration is in areas like Englewood, Austin, and Garfield Park, not tourist zones.
- Plug
- Type A / B · 120V (US standard). No adapter needed for US residents. International visitors need voltage converter for 220V devices unless dual-voltage.
- Timezone
- CST · UTC-6 (CDT UTC-5 mid-March to early November)
A few specific picks.
Hand-picked, not algorithmic. Each of these has earned its space.
A 90-minute docent-led boat tour through downtown's waterways, explaining 50+ buildings and the evolution of the Chicago School. The best single two-hour activity in Chicago — $47, runs April through November. Book ahead on weekends. The docents are architecture-trained and genuinely excellent.
One of the great art museums in the Western Hemisphere. The Impressionist collection (Seurat's *A Sunday on La Grande Jatte*, Grant Wood's *American Gothic*) is world-famous. The Thorne Miniature Rooms are a cult favorite. Allow 3–4 hours minimum.
Anish Kapoor's Cloud Gate ('The Bean') is every bit as photogenic as advertised — the reflections and the underside view reward time. The Frank Gehry Pritzker Pavilion behind it hosts summer concerts (free classical on Wednesdays). Crown Fountain's two pixel-face towers are worth 15 minutes.
Do Chicago deep-dish once, at Lou Malnati's. It's a butter crust, chunky tomato sauce, and a layer of mozzarella that's inverted (cheese below the sauce) — built backwards from thin-crust logic. Split it; one serving is genuinely a meal. Order ahead by 45 minutes; it's not fast food.
A continuous pedestrian promenade along the Chicago River through downtown. Best in the morning before the office traffic and at evening when the bars and restaurants along the river walls open. Free kayak rentals from Chicago Riverwalk at Michigan Ave in summer.
The densest restaurant and bar block in Chicago — from Damen to Wood along Milwaukee Avenue. Cheap Mexican at Big Star, serious Japanese at Mako, wine at The Violet Hour cocktail bar. The neighborhood bleeds into Bucktown with no visible border.
The Mexican-American heart of Chicago's Near South Side — 18th Street from Halsted west is dense with taquerias, panadería (Mexican bakeries), and murals on every block. The National Museum of Mexican Art is free and excellent. Best on a Saturday morning when the markets are open.
The glass-box Ledge observation platforms extend 4 feet out from the 103rd floor, 412 meters up. On a clear day the view extends to four states. Less busy than it sounds — book ahead online. The sense of vertigo is real; the view is worth it.
The Sunday farmers' market on Logan Square Boulevard (May–October) is excellent. The surrounding restaurant strip — Lula Café (26 years in Logan Square, still the neighborhood's soul), Daisies, Giant — is where Chicago's younger chefs landed after Wicker Park rents climbed.
Chicago blues and jazz are two distinct traditions here. Andy's Jazz Club in River North runs nightly. The Chicago Jazz Festival (Labor Day weekend, free, Millennium Park) is the annual event. B.L.U.E.S. on Halsted in Wrigleyville is the long-running blues venue. Book Buddy Guy's Legends in the South Loop for the blues institution.
Pick a neighborhood, not a hotel.
Chicago is a city of neighborhoods. The one you stay in shapes the trip more than the property does.
Different trips for different travelers.
Same city, very different stays. Pick the lens that matches your trip.
Chicago for architecture enthusiasts
Base in the Loop or River North for maximum walking access. River Cruise is non-negotiable. Walking tours from the Architecture Center cover the Michigan Avenue corridor, the Inland Steel Building, the Rookery, and the Marquette Building. Three days of pure architectural tourism is entirely possible here.
Chicago for foodies
Logan Square and Wicker Park for the contemporary scene. Pilsen and Chinatown for the global excellence. One tasting menu — Alinea, Smyth, Ever, or Moody Tongue — if you booked ahead. Grand Central Market for a morning. A Sunday dim sum brunch at MingHin or Phoenix in Chinatown.
Chicago for first-time visitors
Architecture river cruise on day 1. Art Institute and the Bean on day 2. Deep-dish pizza (Lou Malnati's or Giordano's, pick one). Wicker Park for the evening eating and bar scene. Willis Tower Skydeck for the view. Four nights minimum.
Chicago for families with kids
Museum of Science and Industry is the anchor. Lincoln Park Zoo and the lakefront beaches in summer. Navy Pier for rides. Shedd Aquarium and the Field Museum complete the South Loop museum cluster. The L train handles all of these without a car.
Chicago for lgbtq+ travelers
Boystown (Halsted Street in Lakeview) is the traditional center — bars, clubs, and community organizations along a rainbow-flagged stretch. Chicago Pride (late June) is one of the largest in the Midwest. Andersonville (Edgewater) is the quieter, more residential alternative.
Chicago for budget travelers
The L covers everything for $2.50 per ride. Tacos in Pilsen. Dim sum in Chinatown. The Art Institute of Chicago free on Thursdays for Illinois residents; $32 for out-of-staters. Millennium Park, the Riverwalk, and the lakefront are free. Chicago on $90/day is entirely possible.
When to go to Chicago.
A quick year at a glance. Great, good, or skip — see what each month is doing before you book.
The hardest month. Wind chill off the lake makes it brutal. Hotel rates at annual lows. The indoor city (museums, restaurants) is fully operational.
Similar to January. Valentine's Day drives some hotel price spikes. The Polar Vortex events happen in this window. Chicago Restaurant Week (late January/early February) is a good value event.
The Chicago River is dyed green for St. Patrick's Day (parade downtown, March 15–17 area). Still cold but daylight growing noticeably. Architecture tours resume.
The city exhales. Cherry blossoms in Lincoln Park. Rain is common. Architecture river tours restart. Hotel prices still reasonable.
One of the best months. The lakefront comes alive, outdoor dining reopens, and the city is fully energized without summer crowd levels.
Perfect for the lakefront and outdoor Chicago. Chicago Blues Festival (free, early June, Grant Park). Pride parade late June. Beach season begins.
Fourth of July fireworks on the lakefront. Taste of Chicago festival (early July, Grant Park). Hot but the lake breezes help. The most expensive month for hotels.
Lollapalooza (first weekend, Grant Park, 400,000 people) makes that weekend extreme. The beach is at peak season. Hot but manageable. Strong month overall.
One of the best months. Chicago Jazz Festival (free, Labor Day weekend, Millennium Park). Crowds thin, hotel prices ease, the architecture light is extraordinary.
Autumn color in Lincoln Park and the boulevard systems. Chicago Marathon (mid-October, 45,000 runners) closes many downtown streets. The last warm evenings of the year.
The transition to winter arrives. Some outdoor attractions close. The indoor restaurant and museum scene is still excellent. Hotel prices drop significantly.
Christkindlmarket (German Christmas market, Daley Plaza) is atmospheric and worth a cold-weather evening. Ice skating at Millennium Park's McCormick Tribune Plaza. Holiday music at Symphony Center.
Day trips from Chicago.
When you want a change of pace. Each one's a half-day or full-day out, easy from Chicago.
Indiana Dunes National Park
1hSouth Shore commuter train from Millennium Station (1h, $13) to Dune Park. Sand dunes up to 200 feet high dropping directly into Lake Michigan. Surprisingly dramatic landscape 50 miles from downtown. Best June–September.
Galena, Illinois
3hCar rental required (180 miles northwest). Galena is a preserved 1850s lead-mining boom town on the Mississippi River bluffs — 85% of its buildings predate the Civil War. Ulysses S. Grant's home is a museum. Good for a night or two in wine-country Illinois.
Milwaukee
1h 30mAmtrak Hiawatha from Chicago Union Station (1.5h, $25–35). The Milwaukee Art Museum's Calatrava-designed Quadracci Pavilion is architecturally extraordinary. The German brewing heritage (Pabst, Miller Brewery tour). Good for a long day or overnight.
Starved Rock State Park
2hCar or bus tour from Chicago. Eighteen canyons carved by glacial meltwaters, with frozen waterfalls in February and wildflowers in April. One of Illinois' most popular parks — go weekdays. Good with a lodge stay.
Oak Park
30 minGreen Line L to Oak Park (30 min, $2.50). The Frank Lloyd Wright Home and Studio and a self-guided walking tour of 25+ Wright Prairie Style homes — the densest concentration of Wright buildings in the world. Hemingway birthplace museum also here.
Lake Michigan East Shore
2hCar across into Michigan (2h to Harbor Country wine area; 4h to Sleeping Bear Dunes). The Sleeping Bear Dunes National Lakeshore is one of America's most stunning freshwater landscapes. Better as a 2–3 night Michigan road trip than a day trip.
Chicago vs elsewhere.
Quick honest reads on the cities people compare Chicago to.
New York is larger, more internationally diverse, and more relentlessly fast. Chicago is cleaner, cheaper, more walkable in the center, and arguably has better pizza (a contested claim). New York has more everything, but Chicago does everything it does better than New York at a lower price point — the Art Institute vs. the Met, Alinea vs. Eleven Madison Park, the lakefront vs. Central Park.
Pick Chicago if: You want the most sophisticated American mid-size city experience at lower cost — architecture, food, and culture at a more manageable urban scale.
Chicago has a grid and transit; LA has freeways and sprawl. Chicago has genuine seasons — including a winter that will teach you things. LA has year-round warmth and the Pacific Ocean. Chicago is walkable and transit-native; LA requires a car. The food scenes are both excellent; Chicago's is more geographically concentrated.
Pick Chicago if: You want a properly walkable American city with excellent public transit and a dense urban core rather than a car-dependent sprawl.
San Francisco has better natural scenery and a more concentrated dining scene. Chicago has better architecture, better blues and jazz, a more affordable restaurant scene, and a lakefront that rivals the Bay Area without the earthquake risk. SF has the Bay; Chicago has Lake Michigan. Both are significantly cheaper than NYC.
Pick Chicago if: You want Midwest authenticity, great architecture, and a food scene that doesn't require a tech salary to navigate at the mid-range.
Both are Great Lakes cities with strong architecture and food scenes. Toronto is more multicultural and arguably easier to navigate (though Chicago's transit is more frequent). Chicago has more architectural heritage and a deeper music legacy. Toronto has CN Tower and Kensington Market; Chicago has the Loop skyline and the lakefront.
Pick Chicago if: You want the US version of this Great Lakes urban experience — all the architecture and food without crossing an international border.
Itineraries you can start from.
Real plans built by Roamee. Use one as your starting point and change anything.
Architecture river cruise. Art Institute. Millennium Park. Lou Malnati's deep-dish. One Wicker Park evening.
Add Logan Square Sunday market, Pilsen mural walk and tacos, a lakefront bike ride, and one tasting-menu dinner at either Smyth or Alinea if you planned ahead.
All the above plus Hyde Park (Museum of Science and Industry), a jazz evening at Andy's, Chinatown dim sum brunch, the 606 elevated trail through Humboldt Park, and a Blues Brothers pilgrimage.
Things people ask about Chicago.
When is the best time to visit Chicago?
May through June and September through October are the clear picks. Spring: the city emerges from a genuine winter, the lakefront blooms, and temperatures are 15–25°C without summer humidity. Autumn: the same warmth without the festival crowds, and the light through the glass towers at the golden hour is extraordinary. July–August are great for the lakefront and outdoor Chicago (Lollapalooza in August, the beaches, the rooftop bars) but hot and busy. November through March is cold — genuinely, uncompromisingly cold — and only for visitors with a specific purpose.
Is Chicago safe for tourists?
Yes, in tourist areas. The Loop, River North, Lincoln Park, Wicker Park, Bucktown, Logan Square, Pilsen, and the lakefront are all safe by standard urban metrics. Chicago's gun violence problem is concentrated in specific South and West Side neighborhoods that visitors don't have reason to enter. The city's overall violent crime is geographically concentrated in a way that's important to understand: visiting Chicago is not visiting those neighborhoods.
What makes Chicago's architecture special?
After the Great Fire of 1871 destroyed the city, Chicago was rebuilt by a generation of architects who invented the steel-frame skyscraper — allowing buildings to break the previous height limits imposed by masonry walls. Louis Sullivan, Daniel Burnham, William Le Baron Jenney, and later Mies van der Rohe (who moved here in 1938) created what's called the Chicago School of Architecture. The city is essentially a living architecture museum spanning 150 years of the modern tradition. The Architecture Center river cruise ($47) is the most efficient introduction.
What is Chicago deep-dish pizza, and where should I get it?
Deep-dish is more of a pie than a pizza — a butter-pastry crust in a deep pan, cheese laid directly on the crust, chunky tomato sauce on top (inverted from most pizza logic), and a cook time of 30–45 minutes. It's filling to the point of being a challenge for one person. Lou Malnati's is the reliable institution. Giordano's is the stuffed-crust alternative. Pequod's (in Lincoln Park and Morton Grove) has a caramelized crust from the cheese that burns onto the pan. Try it once; most Chicagoans eat thin-crust tavern-style the rest of the time.
How do I get from O'Hare Airport to downtown Chicago?
The CTA Blue Line from O'Hare runs directly to downtown (the Loop) in about 45 minutes for $5 — reliable, frequent, and the easiest option for solo or light-luggage travelers. Rideshares (Lyft, Uber) run $35–55 depending on traffic; the Tri-State/I-90 can be slow during rush hours. Midway Airport (Southwest's hub) is closer — Yellow Line to downtown in 30 minutes, same $5 fare. Avoid the airport taxis unless you have no other option.
Is the Chicago Architecture River Cruise worth it?
Yes — it's one of the best value tourist activities in any American city. The Chicago Architecture Center's guided boat tours ($47, 90 minutes) cover 50+ buildings with docents who are genuinely architecture-trained, not script-readers. The vantage point of the river lets you see buildings from angles impossible on foot. The First Lady boat is the main operator. Book ahead on summer weekends. Walk-in tickets exist but sell out by 11 AM.
What is the best neighborhood in Chicago for food?
Wicker Park / Bucktown for density and range. Logan Square for the newer, chef-driven casual restaurants that are the city's most exciting current wave. Pilsen for Mexican — 18th Street is the strip, and the quality-to-price ratio is unmatched. Chinatown on Cermak for dim sum on weekend mornings. Argyle Street (Uptown) for Vietnamese pho and noodle soups. The problem isn't finding it; it's choosing which type of good you want.
What is the Riverwalk in Chicago?
The Chicago Riverwalk is a continuous pedestrian promenade along the south bank of the Chicago River through downtown — about a mile, lined with restaurant and bar platforms at water level, kayak rentals, boat tour departures, and constant river traffic. It runs from Lake Michigan (where the river briefly reverses into the lake) west to Lake Street. Best at early morning for the quiet reflection on the buildings, and at 6–8 PM when the restaurants fill with after-work crowds.
Is Chicago good for a budget trip?
Better than New York or San Francisco, yes. Budget accommodation in Logan Square or Wicker Park runs $60–90/night in hostels and budget hotels. The L train ($2.50 per ride) covers the city. Many world-class activities are free: Millennium Park, the Chicago Riverwalk, all the lakefront parks and beaches, the 606 Trail, and the Art Institute of Chicago is free for Illinois residents and Chicago teens (out-of-state visitors pay $32). The neighborhood restaurants in Pilsen and Chinatown serve full meals for $10–18.
What is Lollapalooza, and should I plan a trip around it?
Lollapalooza is Chicago's massive annual music festival, held in Grant Park over the first weekend of August for four days. The lineup spans rock, hip-hop, electronic, and pop — historically headlined by names like Billie Eilish, Green Day, Metallica, and Dua Lipa. Around 400,000 people attend over four days. If you're coming for the festival, book hotels 4–6 months ahead. If you're not, avoid Chicago that first August weekend — hotel prices triple and Grant Park is inaccessible.
What are the best free things to do in Chicago?
Millennium Park and Cloud Gate. The lakefront and 18-mile Lakefront Trail. Navy Pier (free entry; rides cost extra). The Chicago Riverwalk. Pilsen's mural walk. The 606 elevated trail through Humboldt Park. Lincoln Park Zoo (always free). All the neighborhood farmers' markets in summer. The Chicago Cultural Center interior (free, stunning Tiffany glass domes). The Museum of Science and Industry is not free but is excellent for families.
How is Chicago's public transit?
Among the best in the US. The L (elevated train) runs 8 lines with 24-hour weekend service and near-24-hour Red and Blue lines on weekdays. Fares are $2.50 per ride or $10/$20/$28 for 1/3/7 day unlimited passes. The Ventra card (reloadable) makes transit easiest. The system covers the Loop, all the major tourist neighborhoods, O'Hare, and Midway airports. Walking is excellent within neighborhoods. You do not need a car in Chicago.
What is Alinea, and is it worth the price?
Alinea is Grant Achatz's modernist restaurant in Lincoln Park, consistently on World's 50 Best lists since 2006. The Gallery (12 courses, $285–395 per person) and the Salon (6 courses, $185–245) tasting menus involve theatrical food presentations — dishes served on suspended spoons, 'edible paintings' made tableside, desserts that defy plate logic. It's a full evening (3–4 hours) and requires booking 2–3 months ahead. Worth it: yes, if you're interested in the chef-as-artist tradition. Wrong place if you want food you recognize.
What's the best way to see Chicago in 3 days?
Day 1: Architecture river cruise in the morning. Millennium Park and the Art Institute in the afternoon. Deep-dish pizza at Lou Malnati's for dinner. Day 2: Lakefront bike ride from Navy Pier north to Montrose Beach. Wicker Park afternoon for lunch and shopping. Evening cocktails at The Violet Hour. Day 3: Pilsen — mural walk and tacos at Nuevo León or a Carnitas El Guero taco stand. Logan Square for a late lunch at Lula Café. Willis Tower Skydeck for the sunset.
What is Chicago-style hot dog, and where do I get one?
A Chicago hot dog is a Vienna Beef hot dog in a poppy-seed bun, topped with yellow mustard, chopped white onions, bright green relish, a dill pickle spear, tomato slices, sport peppers, and celery salt. No ketchup — this is a firm cultural position held by most Chicagoans. Portillo's is the tourist-accessible institution. Superdawg in Norwood Park is the historic drive-in. The dogs at any random Chicago hot dog stand are usually fine, which is the point.
How cold does Chicago get in winter?
Genuinely cold. Average January temperature is −7°C (19°F) with wind chills that push it lower — the 'Polar Vortex' events (2014, 2019) saw −27°C. The wind off Lake Michigan has earned the 'Windy City' label, though locals argue the nickname actually comes from 19th-century political boosterism rather than the weather. If you visit November through March: a real winter coat, base layers, waterproof boots, and gloves are non-optional. Indoor Chicago (museums, restaurants, the L) is excellent year-round.
Is Chicago good for families?
Excellent. The Museum of Science and Industry in Hyde Park is one of the best science museums in the country — full-size WWII German submarine, weather simulation, space module. Lincoln Park Zoo is free and extensive. The Shedd Aquarium is world-class. Millennium Park has the Bean and free summer concerts. Navy Pier has rides and an IMAX. The lakefront beaches (North Avenue Beach, Montrose Beach) are free and swimmable in summer. Chicago is a genuinely family-friendly destination.
What is the 606 Trail in Chicago?
The 606 (formally the Bloomingdale Trail) is an elevated trail on a repurposed 1800s railroad viaduct running 2.7 miles through Wicker Park, Bucktown, Logan Square, and Humboldt Park. Free, open from 6 AM to 11 PM, and one of the best urban infrastructure conversions in the US. It threads through neighborhoods at rooftop level, with access ramps every few blocks. Walking or biking it gives you a completely different spatial reading of the city.
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