Two capitals of the skyscraper: New York and Chicago 2026

A nine-day trip across two cities, late September 2026. Last time I was in the US was 2017, a student internship at UCLA in LA. Nine years later, same person, different coast: New York this time, with three days in Chicago at the end.

This is the working plan I keep for myself, posted so it doesn't get lost and so anyone plotting a similar route can poke around. Dates, where I'm staying, what I'm doing each day, with a Google Maps link for every stop.

Contents:

  1. Before the trip
  2. At a glance
  3. Where I stay
  4. New York
  5. Chicago
  6. What to eat
  7. Booked

Before the trip

Weather. Late September in NYC and Chicago: 22–25 °C in the day, 14–17 °C in the evening. Layering works.

Plugs. Type A/B (two flat prongs). Spain's Type C/E won't fit, so bring an adapter.

Money. Price tags don't include tax: the register adds 8.875% in New York and 10.25% in Chicago. In New York, clothing under $110 is tax-free.

Time. New York is 6 hours behind Barcelona, Chicago 7.

At a glance

Date City Theme
24 Sep, Thu New York Arrival + Astoria
25 Sep, Fri New York Midtown + Yankees
26 Sep, Sat New York HeliNY + Brooklyn
27 Sep, Sun New York MoMA + West Village
28 Sep, Mon New York Astoria Park + Brighton Beach + Vessel
29 Sep, Tue Chicago Fly to Chicago + Grant Park
30 Sep, Wed Chicago Cruise + Art Institute
1 Oct, Thu Chicago Loop + 360
2 Oct, Fri Chicago Fly home

Where I stay

Nights City Area
24–28 Sep New York Airbnb in Astoria, Queens, 3 min from 30 Av on the N/W
29 Sep – 1 Oct Chicago South Loop, by Grant Park, 5 min from the Orange Line

New York

New York. The Dutch founded New Amsterdam here in the 1620s, and it got city rights in 1653. In 1664 the English took it, and Charles II granted the land to his brother, the Duke of York: hence New York.

Sep 24 — Arrival in New York

JFK → Astoria, evening in Times Square.

  • JFK to Astoria — 1. AirTrain JFK → Jamaica Station ($8.50). 2. Jamaica Station → E train (toward World Trade Center). 3. Transfer at Sutphin Blvd–Archer Av → 7 train (toward 34 St-Hudson Yards). 4. 7 train → 74 St-Broadway (or Astoria Blvd, whichever is closer to the Airbnb). 5. Short walk to the apartment. Total ~55 min, ~$11.40 (AirTrain $8.50 + subway $2.90).

  • Times Square — Canyon of screens at night. Walk 42nd to 47th and back, look up. Free.

Sep 25 — Midtown + Yankees

Bryant Park and Grand Central in the morning, Top of the Rock at 10:30, Central Park in the afternoon, Yankees at 17:35.

  • Bryant Park — Pocket park behind the New York Public Library, ringed by skyscrapers. Coffee from a kiosk, office workers cutting through. 20-30 min.

  • Grand Central Terminal — Walk in and look up. Main concourse ceiling: 2,500 stars on turquoise, zodiac constellations in gold. The Whispering Gallery is under the ramp near the Oyster Bar. Free.

  • Chrysler Building lobby — Two minutes east of Grand Central. Red Moroccan marble, ceiling mural of the building itself, elevator doors inlaid with 30 kinds of wood. Free.

  • New York Public Library — The lions outside, then the Rose Main Reading Room on the 3rd floor. Free.

  • St. Patrick's Cathedral — Free, five minutes inside. Between Rockefeller Center and the library.

  • Top of the Rock — Observation deck on the 70th floor of 30 Rockefeller Plaza, the building from Lunch atop a Skyscraper (workers eating lunch on a beam, 1932). Saw the photo, wanted to come here ever since. Both Empire State Building and Central Park fit in this view. Three outdoor levels. Timed entry. 10:30.

  • Central Park — Enter at 59th St & 5th Ave. Walk north: the Pond, Gapstow Bridge, The Mall, Bethesda Fountain, Bow Bridge, Strawberry Fields. About 2 hours.

  • Yankee Stadium — Yankees vs Baltimore Orioles, first pitch 17:35. My first baseball game. Aaron Judge in right field for the home team. 161 St-Yankee Stadium, B/D train from Midtown. Gates open 90 min before first pitch.

Sep 26 — HeliNY + Brooklyn

Helicopter at 10:00 (a gift certificate), then Financial District, Brooklyn Bridge, DUMBO, ferry to Williamsburg, Smorgasburg.

  • Pier 6 Heliport (HeliNY) — The Ultimate Tour, HeliNY's longest route: full Manhattan skyline, Hudson River, Statue of Liberty, Brooklyn Bridge. 18-20 minutes in a Bell 407 with up to five strangers. Arrive 9:30 AM to check in. Only camera, phone, and wallet go on board.

  • Federal Hall — 1789, where Washington took the first presidential oath. Free, two minutes outside.

  • Trinity Church — 1846 neo-gothic, Alexander Hamilton's grave in the churchyard. Free.

  • Oculus — Calatrava, 2016. Walk inside the main atrium: one skylight down the full length, light pours into white space. Free.

  • 9/11 Memorial plaza — Pools sit exactly where the towers stood. Names cut into the bronze edges. Free, no reservation.

  • St. Paul's Chapel — 1766, the only building beside Ground Zero that came through 9/11 intact. Free, five minutes.

  • Brooklyn Bridge — 1883, first steel-wire suspension bridge. Walk the elevated pedestrian path, Manhattan behind, Brooklyn ahead. About 35 min crossing, free.

  • DUMBO / Washington St — Stand between Manhattan Bridge arches, Empire State Building framed in the gap.

  • Brooklyn Heights Promenade — Waterfront esplanade above the highway. Full Manhattan skyline, Brooklyn Bridge, harbor in one sweep.

  • Time Out Market — Bi-level food hall on the DUMBO waterfront. Terrace upstairs has a straight shot at both bridges and the Manhattan skyline.

  • Smorgasburg — Saturdays only, ~80 vendors on the waterfront. Goes until 18:00; show up before 17.

  • Westlight — Rooftop of the William Vale hotel. Manhattan skyline from Brooklyn, at golden hour.

Sep 27 — MoMA + West Village

MoMA in the morning, Lever House and Seagram on Park Ave, Roosevelt Tram, then Greenwich Village, Chelsea Market, High Line, Little Island at sunset.

  • MoMA — Pollock, Warhol's Soup Cans and Gold Marilyn, Lichtenstein's Drowning Girl, Haring's subway-era work, Van Gogh's Starry Night, Picasso's Les Demoiselles d'Avignon, Dalí's melting clocks, Chagall's I and the Village. Permanent collection is 2 solid hours; I could easily spend four. About $30. 10:30.

    Modern art is what I came for, Pollock and Haring first, the rest of the room built around them. The Starry Night is a checkpoint I want to clear, not the headline.

  • Lever House — 1952, the first glass-curtain-wall office building in NYC. Look at it from across Park Ave.

  • Seagram Building — Mies van der Rohe, 1958. Bronze and glass tower set back on a granite plaza with two fountains. Probably the most imitated office building in the world.

  • Roosevelt Island Tramway — Aerial tramway from 59th St & 2nd Ave over the East River. 4 min each way, $2.90 (same as the subway).

  • FDR Four Freedoms Park — On Roosevelt Island. White granite geometry by Louis Kahn, completed 2012. Stark, quiet, the UN building across the water.

  • Washington Square Park — Arch at the bottom of 5th Ave, then the park opens up. Chess hustlers at the tables. NYU students cutting through. Free.

  • Friends building — 90 Bedford St (corner of Grove), the exterior from the TV show. Ten seconds, free.

  • Stonewall Inn — 51 Christopher St. June 1969 raid here started the modern gay rights movement. National Monument now. The facade is nothing special, this one is history.

  • Chelsea Market — Old Nabisco factory, where Oreos were invented in 1898. Los Tacos No. 1 (cash only), The Lobster Place, Mokbar ramen. Daily 7:00-21:00.

  • High Line — 2.3 km elevated park on a decommissioned freight rail line, opened 2009. Enter at 30th St, walk south to Gansevoort. Hudson on your right, sunset behind you.

  • Little Island — Park on 132 concrete tulip-shaped pilings out in the Hudson. Heatherwick, 2021, free. Slope up to the top for sunset.

Sep 28 — Brighton Beach + Vessel

Astoria Park in the morning, then south to Brighton Beach (Russian neighbourhood), boardwalk, Coney Island. Evening back in Manhattan, then Vessel at Hudson Yards.

  • Astoria Park waterfront — Hell Gate Bridge and RFK Bridge overhead, the Manhattan skyline across the water. 15-20 min walk from the Airbnb.

  • Brighton Beach — Brighton Beach Ave under the elevated subway. Russian signs, supermarkets, bakeries. Soviet-era emigre culture.

    Half of why I'm here is the Anora geography: Sean Baker shot parts of the film on this boardwalk, and the Brighton Beach in the movie is the real one. The other half is hearing my own language outside my own kitchen for the first time in nine years. We don't have a Russian neighborhood like this in Barcelona: the diaspora there is spread thin across Vallvidrera and Castelldefels, arrived in the last decade, still speaks Russian to each other, but not on the same block.

  • Tashkent Supermarket — Uzbek halal market. Samsa, lagman, plov, grilled meats to go.

  • Brighton Beach Boardwalk — 2.7 miles of wooden boardwalk, opened 1923. Walk west along the ocean.

  • Coney Island — Wonder Wheel (1920), Cyclone roller coaster (1927).

  • Nathan's Famous — Hot dog with lemonade at 1310 Surf Ave. Required.

  • Vessel — A honeycomb of stairs at Hudson Yards. Free entry, but solo visitors not admitted. D train from Coney Island to 34th St, ~50 min.

Chicago

Chicago. A city since 1837. The name comes from shikaakwa, the Miami-Illinois word for ramps, a wild onion that grew along the shore. In 1871 the Great Chicago Fire destroyed the centre. The city was rebuilt, and in 1885 it got the Home Insurance Building, often called the first skyscraper in the world. Hence the capital of the skyscraper.

Sep 29 — Fly to Chicago + Grant Park

Morning checkout, fly LGA → MDW at 13:25, evening in Grant Park.

  • LaGuardia Airport (LGA) — Subway + Q70 from Jackson Heights-Roosevelt Ave, ~30 min, $2.90.

  • Midway Airport (MDW) — Orange Line CTA to Harold Washington Library station, ~30 min, $2.50. Walk 5 min to the hotel.

  • Grant Park — Buckingham Fountain runs 8:00-23:00 with hourly light shows. Free. Lake east, Loop west.

  • Buckingham Fountain — The fountain in Grant Park. Free.

  • Giordano's — Chicago deep-dish pizza, 3 blocks from the South Loop hotel. Expect 30-45 min wait. Order ahead on the app.

Sep 30 — Cruise + Art Institute

Architecture cruise on the river in the morning, Art Institute in the afternoon.

  • Chicago Architecture Center River Cruise — 90 minutes on the Chicago River, an architecture-school graduate as your guide. Departs from Michigan Ave & Wacker Dr. 10:00.

  • The Art Institute of Chicago — American Gothic, Nighthawks, Water Lilies, A Sunday on La Grande Jatte. Modern Wing by Renzo Piano. 111 S Michigan Ave. About $35, closed Tuesdays only.

Oct 1 — Loop + 360 Chicago

The Loop on foot in the morning, 360 Chicago at sunset.

  • Millennium Park — Get there before 9:00 to see Cloud Gate without the crowd. Jay Pritzker Pavilion by Frank Gehry, Crown Fountain. Free.

  • Cloud Gate ("The Bean") — The mirror bean in Millennium Park. Free.

  • Chicago Cultural Center — 1897. Inside: the largest Tiffany stained glass dome in the world, 38,000 pieces of glass, 11.5m across. Free.

  • The Rookery — 209 S LaSalle St, 1888, Burnham & Root. Lobby reworked by Frank Lloyd Wright in 1905. Free.

  • Federal Center — Mies van der Rohe, 1964. Black steel and glass with Calder's red Flamingo sculpture in the plaza.

  • 360 Chicago (Hancock Center) — 95th floor, views over Lake Michigan and the city grid together. Book ahead for sunset.

    I've been thinking about the view of Chicago and the lake for years. Barcelona has the Mediterranean, but it lies flat at the shore; here the grid runs straight into open water and the city stops. If I do one thing in Chicago, it's this.

  • Au Cheval — Burger spot in West Loop. Expect 1.5-hour queue.

  • Girl & the Goat — Book 1-2 weeks out if you want in.

Oct 2 — Fly home

Last morning and home.

  • Adler Planetarium viewpoint — Walk south through Museum Campus to the tip of the peninsula. Full Chicago skyline across the water, no buildings between you and it. Free.

  • O'Hare Airport (ORD) — Blue Line from any Loop station, ~45 min, $5. International bag drop closes 60 min before departure, leave the hotel by 15:00.

What to eat

New York

  • A bagel with cream cheese and lox.

  • Pastrami on rye, Katz's Delicatessen style.

  • Pizza by the slice, to go.

Chicago

  • Deep-dish, the pizza that's really a pie (Giordano's from the plan).

  • Chicago hot dog: mustard, onion, relish, a pickle spear, tomato, sport peppers, celery salt. No ketchup.

  • Italian beef: thin-sliced roast beef in its own gravy on a roll; The Bear made it famous.

Booked

  • Top of the Rock, Sep 25 — 10:30, $53

  • Yankees vs Orioles, Sep 25 — 17:35

  • HeliNY Ultimate Tour, Sep 26 — 10:00 — gift certificate

  • MoMA, Sep 27

  • Chicago Architecture Center River Cruise, Sep 30 — 10:00, $69

  • The Art Institute of Chicago, Sep 30

Reservations with confirmed dates and times, prices include tax. Everything else on the plan is walk-up.