Shop the Collection

To help you bring a piece of your journey home, we've put together this collection of watercolor studies from our time in Chicago, Illinois. These are our favorite ways to keep the spirit of the trip alive.

Original Series Decorative Magnet

A personal study of Chicago, Illinois, captured in high-fidelity watercolor and prepared for your collection.

Chicago, Illinois | Chicago Skyline At Dusk | Original Series Decorative Magnet
Add to Collection / $18
Exclusive Series Artifact

Original Series Gallery Canvas

This high-fidelity canvas is a beautiful way to anchor a room and keep your memories of Chicago, Illinois fresh long after you've returned home.

Chicago, Illinois | Chicago Skyline At Dusk | Original Series Gallery Canvas detail Chicago, Illinois | Chicago Skyline At Dusk | Original Series Gallery Canvas detail Chicago, Illinois | Chicago Skyline At Dusk | Original Series Gallery Canvas detail Chicago, Illinois | Chicago Skyline At Dusk | Original Series Gallery Canvas detail
Add to Collection / $65

Original Series Hardboard Coaster

A personal study of Chicago, Illinois, captured in high-fidelity watercolor and prepared for your collection.

Chicago, Illinois | Chicago Skyline At Dusk | Original Series Hardboard Coaster
Add to Collection / $18
Exclusive Series Artifact

The Spirit of the Land

Archival Note: Documented personally during our time in Chicago, Illinois. While we leverage a global network of contributors to provide these high-fidelity visual artifacts, each selection is curated to reflect the specific, quiet frequencies we experienced on the ground. These textures serve as a formal study of the unhurried light and environmental character that defined our journey.

Chicago, Illinois study No. 01
Chicago, Illinois / 01 VIA / Bhargava Marripati
The photographer captured Chicago's downtown during the magical hour when city lights begin to glow against a deep purple sky. The warm amber and cool blue lights of the skyscrapers create a striking contrast as they mirror across the still water, while the decorative palm tree lights in the foreground add an unexpected tropical accent to this urban landscape. This moment reveals the quiet elegance of the city after sunset, before the night fully settles in.
Chicago, Illinois study No. 02
Chicago, Illinois / 02 VIA / Pawel aparatem_go
The crisp, bright daylight bathes the cityscape in warm golden tones, creating sharp shadows between the towering skyscrapers. The turquoise waters of Lake Michigan provide a striking contrast to the urban landscape, lending an almost surreal quality to this elevated perspective. Standing at this vantage point would offer a breathtaking sense of scale and density, revealing the intricate geometry of one of America's greatest cities.
Chicago, Illinois study No. 03
Chicago, Illinois / 03 VIA / Julia Filirovska
This photo captures an iconic Chicago deep-dish pizza served in a traditional cast iron skillet, its golden-brown crust glistening under warm light. The vibrant orange-red peppers arranged on top create a striking contrast against the rich, bubbly cheese surface. Often overlooked is the subtle sheen of oil pooling in the skillet's wells, a hallmark of authentic Chicago-style pizza that contributes to its distinctive crispy, caramelized crust.

Where to wander

Archival Note: A curated field study of Chicago, Illinois, prioritizing cultural relevance and archival merit. These locations have been meticulously researched and vetted to ensure they represent the most authentic atmosphere for your own expedition.

Local Cuisine Spotlight
This Chicago French dip features succulent shredded beef piled high on a buttery croissant, crowned with caramelized peppers and melted cheese. The accompanying au jus, aromatic and deeply savory, invites each bite to be dipped into pure comfort. Enjoyed against the backdrop of the city skyline, this sandwich embodies the perfect marriage of Chicago hospitality and timeless bistro tradition.
Credits: THE PAINTED PASSPORT
Local cuisine study in Chicago, Illinois

☕︎ Local Flavor

Girl and the Goat

Rating: 5* | Price: $$$ | Coordinates: 41.8836, -87.6484

Chef Stephanie Izard's flagship restaurant in Fulton Market is a celebration of bold, globally inspired flavors built around wood-fired cooking and seasonal ingredients. The menu is designed for sharing, so come hungry and order generously with your whole table. The goat empanadas and wood-roasted pig face have become legendary dishes that keep diners returning again and again.

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Lou Malnati's Pizzeria

Rating: 5* | Price: $$ | Coordinates: 41.8902, -87.6338

No Chicago visit is complete without a deep-dish pizza from Lou Malnati's, a beloved institution that has been serving the city since 1971. The buttery, flaky crust cradles a generous layer of chunky tomato sauce and thick Wisconsin mozzarella that stretches with every glorious bite. Arrive early or expect a wait, because locals and visitors alike line up enthusiastically for a table.

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Avec

Rating: 5* | Price: $$$ | Coordinates: 41.8836, -87.6476

Avec is a cozy, communal wine bar and restaurant in the West Loop that has influenced Chicago dining for over two decades with its Mediterranean-inspired small plates. The chorizo-stuffed medjool dates wrapped in bacon are an absolute must-order and have earned near-mythical status among regulars. The intimate wooden interior fills quickly, so arriving right when doors open is a smart and rewarding strategy.

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The Purple Pig

Rating: 4* | Price: $$ | Coordinates: 41.8913, -87.6254

Perched along Michigan Avenue, The Purple Pig is a cheerful, charcuterie-driven spot that takes obvious delight in celebrating every part of the pig. The menu reads like a love letter to Mediterranean flavors, with crispy fried cheeses, cured meats, and vibrant vegetable dishes that shine just as brightly. Outdoor seating with views of the Magnificent Mile makes this a particularly perfect lunch destination on a sunny Chicago afternoon.

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🛌︎ Boutique Stays

The Langham Chicago

Rating: 5* | Price: $$$$ | Coordinates: 41.8868, -87.6272

Nestled along the Chicago River in a stunning Mies van der Rohe building, The Langham offers breathtaking water views from nearly every room. The spa is among the finest in the city, featuring a gorgeous indoor pool wrapped in warm light. Guests consistently rave about the attentive service and the elegant afternoon tea experience.

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Virgin Hotels Chicago

Rating: 4* | Price: $$$ | Coordinates: 41.8969, -87.6217

Virgin Hotels brings a playful, design-forward energy to the heart of the Loop, making it a favorite among creative travelers. Rooms called Chambers are cleverly divided into a dressing area and a cozy sleeping nook. The rooftop bar buzzes with locals on warm evenings, offering skyline views that are genuinely hard to beat.

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Ace Hotel Chicago

Rating: 4* | Price: $$$ | Coordinates: 41.8851, -87.6478

Set in the vibrant Fulton Market district, Ace Hotel Chicago blends industrial charm with warm, curated interiors that feel both stylish and lived-in. The lobby doubles as a social hub where guests mingle over locally roasted coffee throughout the day. Its walkable location puts you steps from some of the city's most exciting restaurants and art galleries.

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The Gwen Chicago

Rating: 5* | Price: $$$$ | Coordinates: 41.8963, -87.6267

Located on the Magnificent Mile, The Gwen is a beautifully restored luxury hotel that honors Chicago's rich architectural heritage with thoughtful Art Deco details. The rooms are spacious and serene, decorated in soft neutral tones that invite genuine relaxation after a day of exploring. The in-house steakhouse offers a refined dining experience worthy of a special evening.

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📍︎ Field Study

The Art Institute of Chicago

Rating: 5* | Price: $$ | Coordinates: 41.8796, -87.6237

One of the greatest art museums in the world, the Art Institute of Chicago houses an extraordinary collection spanning thousands of years and dozens of cultures under its iconic Beaux-Arts roof. Seurat's pointillist masterpiece and Grant Wood's American Gothic draw crowds, but the Asian and decorative arts galleries offer quieter moments of equal wonder. Plan at least half a day here because the building rewards slow, unhurried exploration at every turn.

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Millennium Park

Rating: 5* | Price: Free | Coordinates: 41.8827, -87.6233

Millennium Park is the beating heart of downtown Chicago, anchored by Anish Kapoor's reflective Cloud Gate sculpture that visitors affectionately call the Bean. Summer concerts at the Jay Pritzker Pavilion fill the lawn with music and laughter on warm evenings, creating a genuinely communal atmosphere. The park connects seamlessly to the lakefront trail, making it a perfect starting point for a long waterfront stroll.

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Chicago Riverwalk

Rating: 5* | Price: Free | Coordinates: 41.8877, -87.6279

The Chicago Riverwalk stretches nearly a mile along the main branch of the Chicago River, offering stunning views of the city's world-famous architecture from a unique ground-level perspective. Kayak rentals, open-air bars, and fresh seafood kiosks line the path, making it easy to spend an entire afternoon wandering without a plan. Architecture boat tours depart from here regularly and provide one of the most memorable ways to understand Chicago's skyline.

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Wrigley Field

Rating: 5* | Price: $$ | Coordinates: 41.9484, -87.6553

Wrigley Field is one of the oldest and most beloved ballparks in America, carrying over a century of baseball history within its ivy-covered brick outfield walls. Even if you are not a dedicated Cubs fan, the atmosphere on game day in the surrounding Wrigleyville neighborhood is electric and thoroughly infectious. Grab a hot dog, find your seat in the sun, and let the easy rhythm of a summer afternoon game wash completely over you.

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Typography

Archival Note: A formal technical study of Chicago, Illinois, archiving the coordinates, elevation, and environmental data that define the region. This data serves as a vital record for our ongoing global field study, providing the technical foundation behind every atmospheric detail captured in our visual work.

Botanical and pigment specimen study for Chicago, Illinois Colors of Chicago, Illinois
Coordinates
41.8781° N, 87.6298° W — Chicago, Illinois, situated on the southwestern shore of Lake Michigan in the American Midwest
Historical Epoch
Incorporated in 1837 and rebuilt with ambition after the Great Fire of 1871, Chicago became the laboratory where the modern skyscraper was invented and the American city was reimagined in steel and glass.
Elevation
176 m / 577 ft - Chicago sits at near lake level on the flat glacially formed plain of northeastern Illinois, with minimal elevation variation across the city grid
Atmosphere
Dfa, Hot-Summer Humid Continental. Chicago swings hard between hot, humid summers and genuinely brutal winters. Spring and fall are glorious but brief, and the lake shapes everything.
Observation Hour
07:15. The early morning light over Lake Michigan in summer arrives low and golden across the water, catching the glass of the skyline with extraordinary warmth before the haze builds. Max 220 chars.
Primary Pigment
Lake Michigan Slate (#5B7FA6) and Chicago Brick Amber (#C4813A)
Best Time to Visit
June through September - the city bursts into outdoor life with festivals, lakefront activity, rooftop bars, and warm evenings that make the architecture feel even more spectacular.
Avoid Visiting
January through February - polar vortex conditions, wind chill temperatures well below freezing, and minimal outdoor appeal make these the months only the committed should brave.

The Local Tongue

Language is the invisible architecture of Chicago, Illinois. These entries document the regional vocabulary—capturing the "texture" of local speech that standard translations often miss. Hand-curated expressions reflecting the specific spirit and daily rhythm of the region.
Archival study of English cultural texture

via / Airam Dato-on

Primary Language English
Regional Dialect Chicago English, Midwest American

The L

The L refers to the elevated rail network that loops around the downtown core and threads through every major neighborhood. Chicagoans orient their entire city by which line runs closest, and the screech of steel on the elevated tracks above Wabash Avenue is as much a part of the city soundtrack as any blues guitar.

Dibs

Dibs is the local custom of placing a chair or plastic bin in a street parking spot after shoveling it out following a snowstorm, a wordless but universally understood claim of ownership. It is a practice that captures the Chicago character perfectly, part stubbornness, part practicality, and entirely the product of winters that demand residents earn every small comfort.

Frunchroom

Frunchroom is a Chicago working-class contraction of front room, meaning the living room kept tidy for guests and rarely used by the family itself. It speaks to the particular domestic culture of the bungalow belt neighborhoods, where Polish, Italian, and Irish families built tight blocks of modest homes and maintained a formality in the front of the house that the bustling kitchen in the back never required.

Wait! before you go...

Before you head over to Chicago, Illinois, we wanted to share a few basic tips we picked up along the way. These notes cover the simple things—like how to get around or what to do about cash—so you can spend less time worrying and more time just enjoying the place.
🚲 Getting Around The Chicago Transit Authority operates the L train network and an extensive bus grid covering the city and many suburbs. The L is the fastest and most atmospheric way to move between neighborhoods, and a Ventra card loaded with credit is the essential tool for any visit.
⚖️ Cash or Card Chicago is almost entirely card-friendly, with contactless payments accepted at the vast majority of restaurants, bars, shops, and transit fare machines. A small amount of cash is useful for tipping at casual spots, buying from street vendors or farmers markets, and occasionally for valet parking in the city center.
☁️ Good to Know Chicagoans will ask what neighborhood someone lives in before almost any other question, and giving a specific answer rather than just saying the north side or the south side earns immediate respect. The city's identity is deeply geographic and each neighborhood carries its own history, cuisine, and character that locals take genuine pride in explaining.
🏧 ATMs ATMs are extremely abundant throughout Chicago, found in bank branches, convenience stores, hotels, and grocery stores in every neighborhood. Major bank ATMs such as Chase, Bank of America, and Wells Fargo charge no fees to their own customers, while independent ATMs in bars and smaller shops typically charge between two and four dollars per transaction.
💳 Currency The United States Dollar is the only currency in use, and prices in Chicago are consistent with major American city standards. Tipping culture is strong and expected: 18 to 20 percent at restaurants, a dollar or two per drink at bars, and similar courtesy for any service staff.
🔌 Plugs Type A and Type B outlets, operating at 120V and 60Hz. International visitors will need a voltage converter for devices not rated for dual voltage.
🛡️ Safety Chicago has neighborhoods with elevated crime rates, primarily on the far south and west sides well outside the areas most visitors explore, and the tourist and dining corridors are generally very safe with normal urban awareness. Staying alert on the L late at night, keeping phones out of sight in crowded areas, and not leaving valuables visible in parked cars are sensible habits in any major American city.
✈️ Airports O'Hare International Airport (ORD) is the primary hub located about 17 miles northwest of downtown, handling the majority of domestic and international flights and connected directly to the city center by the Blue Line L train. Midway Airport (MDW) on the southwest side serves many budget carriers and is a shorter drive from the Loop, also connected by the Orange Line L.

Behind The Scenes

Nathan

Note from the Founder

Hey, did you know this fun fact about Chicago, Illinois? Chicago reversed the flow of the Chicago River in 1900, an engineering feat designed to push sewage away from Lake Michigan. The project remains one of the most audacious public works achievements in American history.
Thank you for exploring the Chicago, Illinois series with us. We hope these notes have inspired you to add this incredible destination to your own passport—we are so glad you're here. Nathan's signature

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