Chicago, USA
The Bear (Hulu series) focused on a fine-dining restaurant in Chicago, and its cinematography fetishized the city's food…
Best Time: May–September (warm, no brutal winter wind)
Daily Budget: $60–100 (accommodation $50–80, food $15–30, activities $5–15, transport $5)
Getting There: Fly to Chicago (major hub with multiple airports)
Visa: Visa-free for most nationalities (ESTA for UK/EU citizens)
Currency: US dollar
Language: English; some neighborhoods have secondary languages
Why Go
The Bear (Hulu series) focused on a fine-dining restaurant in Chicago, and its cinematography fetishized the city's food culture, architecture, and grittiness. Chicago has always been a major restaurant city (Alinea, Frontera Grill, small neighborhood bistros), but the show amplified interest.
Beyond restaurant culture, Chicago has architecture (Frank Lloyd Wright homes, the Loop skyscraper corridor), a serious jazz legacy, Lake Michigan beaches, deep-dish pizza debates, Italian beef sandwiches, and a genuinely hard-working, generous vibe that feels different from coastal cities.
The best version of Chicago is food-focused and architectural. Take the river architecture cruise, visit Wright's home in Oak Park, eat at neighborhood joints, and walk the Magnificent Mile. You can do Chicago in a 3–4 day trip and have a complete experience.
Top Experiences
Chicago River architecture cruise: Learn about skyscrapers from the water. 1–2 hour cruise. $42–65. Sunset cruises are golden-hour magic. Departs from downtown.
Frank Lloyd Wright home tours (Oak Park): Tour the architect's home and surrounding neighbourhood. Frank Lloyd Wright Home & Studio $15 entry, 1-hour guided tour. Other Wright homes nearby ($15 each). Full morning activity.
Deep-dish pizza at small shops: Skip the chain pizza places. Go to a neighborhood place (Pequod's, Nancy's, or local spots in your neighborhood). Deep-dish pizza $6–12 per slice depending on toppings.
Alinea fine dining (if budget allows): World-famous modernist restaurant. Tasting menu $195–295. Reserve months in advance. A Bear-adjacent experience that justifies the cost.
Where to Stay
Budget:: Hotels in neighborhoods away from downtown (Wicker Park, Pilsen). $50–70/night.
Mid-Range:: Downtown or river-view hotels. $80–120/night.
Splurge:: Luxury hotel or historic boutique property. $150–250/night.
What to Eat
Italian beef sandwich: Thinly sliced seasoned beef on a roll, often dipped in gravy. Al's Beef, Portillo's, or small shops. $6–10.
Deep-dish pizza: Chicago's signature. Pequod's, Nancy's, or local joints. $8–15 per slice for large.
Chicago-style hot dog: Mustard, onions, relish, peppers, tomatoes, no ketchup. Relevant for debate. $2–4.
Jibarito: Puerto Rican-inspired sandwich with plantain instead of bread. Pilsen neighborhood. $8–12.
Fresh fruit from farmers markets: Union Station Sunday market. $2–6 depending on season.
Plan & budget
Getting there
Fly to Chicago (major hub with multiple airports)
Daily budget
$60–100 (accommodation $50–80, food $15–30, activities $5–15, transport $5)
Best time
May–September (warm, no brutal winter wind)
Insider Tip
Neighborhoods like Pilsen, Wicker Park, and Logan Square have better restaurants and less tourist markup than downtown. Take the El train to feel like a local (and it's cheap). River architecture cruise is the one touristy thing worth doing. If you can't get into Alinea, other fine-dining spots (Oriole, Smyth) exist but are less legendary. Winter (November–March) is brutal (wind is real); come in warmer months. The Bear is set in fine dining; visit both fancy restaurants and street-food spots for full picture.
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