Chicago

Day 1: Skyline icons, river views and a night at the theatre

Ease into Chicago’s dual personality: pragmatic grit and unpretentious sophistication. You’ll see statement architecture up close, then swap river breezes for gallery calm before a classic night out.

• Morning: Ride the Brown Line ‘L’ around the Loop for the architectural canyon views, then wander Millennium Park while it’s quiet; see Cloud Gate before fingerprints and crowds build, and check Crown Fountain if it’s warm. Pop into the Chicago Cultural Center for the Tiffany dome (free) and, if the wind bites, duck through the Pedway between buildings.
• Midday: Join the Chicago Architecture Center river cruise (book ahead; best light late morning). Afterwards stroll the Riverwalk for lunch by the water, or head to the Chicago Athletic Association’s Cindy’s for lake-and-park views without an observation-deck fee.
• Afternoon: Spend a focused couple of hours at the Art Institute (enter via the Modern Wing to skip queues); pick one or two areas—Impressionists or the Thorne Rooms—and linger. If weather turns, add the Rookery or Marquette Building lobbies for historic interiors.
• Evening: Dinner in the West Loop/Fulton Market (reserve—this is peak); then choose a show: big musical downtown, intimate drama at Steppenwolf, or improvisation at Second City. Nightcap in Old Town Ale House or a blues club if you’ve still got fuel.

Day 2: Neighbourhood mosaic—murals, markets and Chicago blues

Today is about the city of 77 neighbourhoods: hyper-local pride, great food and street-level culture. Use the ‘L’ and your Ventra—this is how locals hop between scenes.

• Morning: Coffee and a pastry on Milwaukee Avenue in Wicker Park, then browse record and book shops. If it’s Saturday, detour to Logan Square’s farmers’ market (summer) before an early tavern‑style pizza slice—locals eat it thin and square‑cut.

By Air

• O’Hare International (ORD): ~27 km/17 miles NW of the Loop. CTA Blue Line to downtown: 45–60 minutes, 24/7. Taxi/ride-hail: 30–90 minutes depending on traffic. Major hub for United and American with extensive domestic and long‑haul international flights.
• Midway (MDW): ~16 km/10 miles SW of the Loop. CTA Orange Line to downtown: 25–30 minutes. Taxi/ride-hail: 20–45 minutes. Primary base for Southwest with broad US coverage.
• Alternatives:
  • Milwaukee Mitchell (MKE): ~137 km/85 miles north. Amtrak Hiawatha to Union Station ~1 h 25; coach 1.5–2 h; driving 1.5–2 h.
  • Rockford (RFD): ~145 km/90 miles NW, limited low‑cost flights; driving/shuttle 1.5–2 h.
  • South Bend (SBN): ~155 km/96 miles east; South Shore Line to Millennium Station ~2.5–3 h; driving ~2–2.5 h.

By Train

• Union Station (Canal St): Chicago’s Amtrak hub with frequent regional and long‑distance services.
  • Key routes (typical times): Milwaukee (Hiawatha ~1 h 25), St Louis (Lincoln Service ~4.5–5.5 h), Detroit/Pontiac (Wolverine ~4.5–5.5 h), Grand Rapids (Pere Marquette ~4 h), Minneapolis–St Paul (Empire Builder ~7.5–8 h to MSP), Kansas City (~7.5 h), Washington DC (Capitol Limited ~17 h), New York/Boston (Lake Shore Limited ~19–21 h), New Orleans (City of New Orleans ~19 h), West Coast routes to Los Angeles (Southwest Chief/Texas Eagle) and San Francisco Bay Area (California Zephyr).

Overall vibe: Big-city energy without the big-city crush—Chicago blends pragmatic grit and polished culture in friendly, less-crowded neighbourhoods that reward curiosity and value.

• A mosaic of 77 neighbourhoods where “Midwestern nice” meets no-nonsense charm; think unpretentious sophistication, straight-talking locals, and serious culture without the queues or price tag.
• Architecture you can actually savour: loop the ‘L’ on the Brown Line, stroll the Riverwalk, pop into the free Chicago Cultural Center for the Tiffany dome, or catch Cloud Gate at sunrise—iconic, accessible, and uncrowded at the edges.
• Eat like a local for less: Italian beef “dipped,” tavern‑style pizza cut in squares, a no‑ketchup hot dog, and superb Mexican in Pilsen or Vietnamese on Argyle; BYOB spots and corner taps keep quality high and costs low (bonus: try the Chicago Handshake—Malört + Old Style).
• Nights with soul and space: blues after midnight at Buddy Guy’s Legends or Kingston Mines, house music roots in intimate clubs, comedy at The Second City; summers burst with lakefront festivals, winters turn cosy—with quirky traditions like “dibs” on shoveled parking.

Bold, big-hearted and brilliantly down‑to‑earth, Chicago suits travellers who love world‑class culture without the faff. It mixes pragmatic grit with unpretentious sophistication, from iconic architecture to neighbourhood‑driven food, music and art. Easy to roam by the 'L' and along the lakefront, it shines in summer festivals and turns wonderfully cosy in winter.

• History lovers: Trace the city’s resilience from the Great Fire to Bronzeville on walking tours, river cruises and at the Chicago History Museum.
• Architecture & design fans: Marvel at skyline greats on the CAC river cruise, explore Frank Lloyd Wright gems, and ascend Willis (Sears) Tower for classic views.
• Foodies: Eat across 77 neighbourhoods—from Italian beef and tavern‑style pizza to Michelin‑starred tasting menus—often better value than New York.
• Music & nightlife: Hear electrified blues and the birthplace of house, slip into speakeasies, and dance in late‑licence clubs that go to 4am.
• Art & culture seekers: See masterpieces at the Art Institute, free exhibitions at the Cultural Center, and public icons like Cloud Gate and the Picasso.
• Active travellers & sports fans: Cycle the 18‑mile Lakefront Trail, hit city beaches, then cheer the Cubs at Wrigley Field for a proper local rite.

These are the unmissable highlights of Chicago—essential experiences that showcase its grit, creativity, and skyline drama. Tick these off to feel the city’s true character beyond the Loop.

• Walk the Lakefront Trail from Grant Park to the Museum Campus for sweeping skyline-and-lake views.
• Explore vibrant neighbourhoods—Pilsen’s murals, Devon Avenue’s South Asian shops, and Asia on Argyle’s eateries.
• Visit Millennium Park’s Cloud Gate and the Art Institute to pair modern spectacle with world-class masterpieces.
• Take the Chicago Architecture Center river cruise to see 140 years of skyscraper innovation from the water.
• Hike the 606 (Bloomingdale Trail), an elevated greenway linking parks, public art, and chilled cafés across the Northwest Side.

These are the unmissable highlights of Chicago—essential experiences that showcase its grit, creativity, and skyline drama. Tick these off to feel the city’s true character beyond the Loop.

• Walk the Lakefront Trail from Grant Park to the Museum Campus for sweeping skyline-and-lake views.
• Explore vibrant neighbourhoods—Pilsen’s murals, Devon Avenue’s South Asian shops, and Asia on Argyle’s eateries.
• Visit Millennium Park’s Cloud Gate and the Art Institute to pair modern spectacle with world-class masterpieces.
• Take the Chicago Architecture Center river cruise to see 140 years of skyscraper innovation from the water.
• Hike the 606 (Bloomingdale Trail), an elevated greenway linking parks, public art, and chilled cafés across the Northwest Side.

Chicago’s food culture is big on flavour and low on fuss: immigrant roots, working‑class classics and chef‑driven innovation sit side by side. Expect hearty sandwiches, iconic pizzas and street‑corner stands, plus buzzing markets and bars. You’ll eat well at a counter, in a pub, or on a sunny patio by the lake.

• Italian beef sandwich – thin‑sliced beef in savoury jus, ordered “wet” or “dipped”, with hot giardiniera or sweet peppers. Best devoured standing at steamy counter joints.

• Chicago‑style hot dog – all‑beef on a poppy‑seed bun “dragged through the garden” (mustard, relish, onion, tomato, pickle, sport peppers, celery salt); never ketchup. Perfect from retro kiosks after a match or gig.

• Deep‑dish pizza – buttery crust layered with mozzarella and bright tomato sauce; a slow, indulgent slice of local history. Settle into classic pizzerias and expect queues.

• Chicago Handshake – a shot of Malört with an Old Style beer; bitter, bracing, and proudly local. Best attempted in laid‑back dive bars with plenty of banter.

Choosing the right area in Chicago will shape your trip more than the hotel itself. Pick a base for the vibe and convenience you want—each neighbourhood has its own scene, pace, and price point.

• The Loop — skyscraper canyons, riverwalk and big‑ticket museums; super‑central with easy ‘L’ access, great for first‑timers and architecture lovers, quieter after office hours.
• River North — buzzy dining, bars and galleries by the Magnificent Mile; suits nightlife seekers and shoppers who want energy late into the night.
• West Loop (Fulton Market) — industrial‑chic warehouses turned award‑winning restaurants and cocktail spots; ideal for foodies and trend‑hunters.
• Lincoln Park — leafy streets by the lake, free zoo and indie shops; calm, residential feel that’s perfect for families and morning joggers.

Choosing the right area in Chicago will shape your trip more than the hotel itself. Pick a base for the vibe and convenience you want—each neighbourhood has its own scene, pace, and price point.

• The Loop — skyscraper canyons, riverwalk and big‑ticket museums; super‑central with easy ‘L’ access, great for first‑timers and architecture lovers, quieter after office hours.
• River North — buzzy dining, bars and galleries by the Magnificent Mile; suits nightlife seekers and shoppers who want energy late into the night.
• West Loop (Fulton Market) — industrial‑chic warehouses turned award‑winning restaurants and cocktail spots; ideal for foodies and trend‑hunters.
• Lincoln Park — leafy streets by the lake, free zoo and indie shops; calm, residential feel that’s perfect for families and morning joggers.

Chicago is an easy city to navigate, with a simple grid, good public transport and a compact core anchored by the lakefront. A few practical details will help you plan smoothly and avoid peak-price moments.

• Affordability: Expect casual meals from about £12–£20, mid‑range dinners £30–£50, Michelin/tasting menus £100+; mid‑range city‑centre hotels typically run £120–£220 per night, with rates spiking for big events.
• Transport: Walk the Loop, riverwalk and lakefront, but use the ‘L’ (from both O’Hare and Midway), buses and contactless Ventra passes for distance; Metra trains suit suburban day trips, Divvy bikes are handy in warmer months, seasonal water taxis run the river, and driving/parking downtown is costly so skip the car unless you’re heading out of town.
• Language: English is the main language and widely understood by visitors; you’ll also hear plenty of Spanish, and tourist signage is clear in key areas.
• Safety & comfort: Central neighbourhoods feel generally safe with normal big‑city awareness (keep bags zipped on busy trains); the city is family‑ and solo‑friendly, winters are very cold (dress in layers), summers are warm and lively, and late at night it’s sensible to stick to main streets or use ride‑hailing.
• Crowds: Peak season is June–August (festivals, beach weather), shoulder months May and September–October are ideal, winter is quiet (except holidays and St Patrick’s Day), and conventions or game days can swell crowds and prices around the Loop, West Loop, Wrigleyville and the Museum Campus.

Chicago is an easy city to navigate, with a simple grid, good public transport and a compact core anchored by the lakefront. A few practical details will help you plan smoothly and avoid peak-price moments.

• Affordability: Expect casual meals from about £12–£20, mid‑range dinners £30–£50, Michelin/tasting menus £100+; mid‑range city‑centre hotels typically run £120–£220 per night, with rates spiking for big events.
• Transport: Walk the Loop, riverwalk and lakefront, but use the ‘L’ (from both O’Hare and Midway), buses and contactless Ventra passes for distance; Metra trains suit suburban day trips, Divvy bikes are handy in warmer months, seasonal water taxis run the river, and driving/parking downtown is costly so skip the car unless you’re heading out of town.
• Language: English is the main language and widely understood by visitors; you’ll also hear plenty of Spanish, and tourist signage is clear in key areas.
• Safety & comfort: Central neighbourhoods feel generally safe with normal big‑city awareness (keep bags zipped on busy trains); the city is family‑ and solo‑friendly, winters are very cold (dress in layers), summers are warm and lively, and late at night it’s sensible to stick to main streets or use ride‑hailing.
• Crowds: Peak season is June–August (festivals, beach weather), shoulder months May and September–October are ideal, winter is quiet (except holidays and St Patrick’s Day), and conventions or game days can swell crowds and prices around the Loop, West Loop, Wrigleyville and the Museum Campus.

In Chicago, the seasons are pronounced: frigid, windy winters; glorious, festival‑packed summers; and brief, changeable springs with colourful autumns. Crowds and prices peak in summer and ease right off in winter.

• High Summer (Jun–Aug): Hot and often humid; festivals everywhere, packed lakefront and rooftops; highest prices and biggest crowds; exuberant vibe.
• Shoulder Season (Apr–May, Sep–Oct): Milder but changeable; fewer crowds and better value; blossom or autumn colour and lively neighbourhoods—best balance.
• Winter (Nov–Mar): Very cold with snow and “The Hawk” winds; lowest prices and shortest queues; indoor culture, cosy bars and holiday lights; gritty, resilient mood.

In Chicago, the seasons are pronounced: frigid, windy winters; glorious, festival‑packed summers; and brief, changeable springs with colourful autumns. Crowds and prices peak in summer and ease right off in winter.

• High Summer (Jun–Aug): Hot and often humid; festivals everywhere, packed lakefront and rooftops; highest prices and biggest crowds; exuberant vibe.
• Shoulder Season (Apr–May, Sep–Oct): Milder but changeable; fewer crowds and better value; blossom or autumn colour and lively neighbourhoods—best balance.
• Winter (Nov–Mar): Very cold with snow and “The Hawk” winds; lowest prices and shortest queues; indoor culture, cosy bars and holiday lights; gritty, resilient mood.

Day 3: Lakefront, museums and rooftops (or baseball)

Open with big sky and big water, then pick culture or sport and wrap with a view. Summer is outdoorsy and festival‑heavy; winter leans cosy, with hearty classics and underground shortcuts.

• Morning: Walk or cycle a stretch of the Lakefront Trail—Grant Park to the Museum Campus has the postcard skyline. If it’s brisk, head straight into the Field Museum or Shedd; on clear days, the Adler shoreline gives the best skyline photo.
• Midday: Dim sum or noodles in Chinatown, or Vietnamese sandwiches on Argyle; if you’re central, grab Italian beef—order it “dipped, hot” if you like a messy classic. On blustery days, warm up by exploring the Loop’s historic lobbies (and the Pedway).
• Afternoon: Browse the Magnificent Mile and the Tribune/Wrigley Building river gate, then duck into the Chicago Cultural Center for rotating exhibitions. Sports fans in summer: go north for a Cubs game at Wrigley Field; in colder months, swap in the Museum of Contemporary Art or a Devon/Andersonville indie‑shop stroll.
• Evening: Toast the city from a skyline perch—the Signature Lounge (96th) is a savvy swap for an observation deck, or pick a West Loop rooftop in fair weather. For live music, slide to the Green Mill for late jazz (weeknights feel most local); night owls can find 4am bars on weekends—plan your ride home in advance.

By Bus

• Intercity operators (FlixBus, Greyhound, Megabus) run to Milwaukee (~1.5–2 h), Madison (~3–3.5 h), Indianapolis (~3–3.5 h), Detroit (~5–6 h), St Louis (~5–6 h), Minneapolis (~8–9 h), and more.
• Most services use curbside stops around the West Loop/Union Station area and other downtown locations. Check your ticket for the exact pick‑up/drop‑off point; there is no single central bus terminal.

By Car

• Main approaches: I‑90/94 (Kennedy/Dan Ryan), I‑290 (Eisenhower), I‑55 (Stevenson), I‑57, I‑80/I‑94, and I‑294 (Tri‑State Tollway). Illinois Tollway roads use I‑PASS/pay‑by‑plate.
• Typical drives in light traffic: Milwaukee 1.5–2 h (145 km/90 miles); Madison 2.5–3 h (240 km/150 miles); Indianapolis 3–3.5 h (300 km/185 miles); Detroit 4.5–5.5 h (450 km/280 miles); St Louis 4.5–5.5 h (480 km/300 miles); Minneapolis 6.5–7.5 h (640 km/400 miles).
• Expect heavy congestion at peak times and high downtown parking costs. Winter weather can significantly affect travel times.

Bold, big-hearted and brilliantly down‑to‑earth, Chicago suits travellers who love world‑class culture without the faff. It mixes pragmatic grit with unpretentious sophistication, from iconic architecture to neighbourhood‑driven food, music and art. Easy to roam by the 'L' and along the lakefront, it shines in summer festivals and turns wonderfully cosy in winter.

• History lovers: Trace the city’s resilience from the Great Fire to Bronzeville on walking tours, river cruises and at the Chicago History Museum.
• Architecture & design fans: Marvel at skyline greats on the CAC river cruise, explore Frank Lloyd Wright gems, and ascend Willis (Sears) Tower for classic views.
• Foodies: Eat across 77 neighbourhoods—from Italian beef and tavern‑style pizza to Michelin‑starred tasting menus—often better value than New York.
• Music & nightlife: Hear electrified blues and the birthplace of house, slip into speakeasies, and dance in late‑licence clubs that go to 4am.
• Art & culture seekers: See masterpieces at the Art Institute, free exhibitions at the Cultural Center, and public icons like Cloud Gate and the Picasso.
• Active travellers & sports fans: Cycle the 18‑mile Lakefront Trail, hit city beaches, then cheer the Cubs at Wrigley Field for a proper local rite.

Chicago’s food culture is big on flavour and low on fuss: immigrant roots, working‑class classics and chef‑driven innovation sit side by side. Expect hearty sandwiches, iconic pizzas and street‑corner stands, plus buzzing markets and bars. You’ll eat well at a counter, in a pub, or on a sunny patio by the lake.

• Italian beef sandwich – thin‑sliced beef in savoury jus, ordered “wet” or “dipped”, with hot giardiniera or sweet peppers. Best devoured standing at steamy counter joints.

• Chicago‑style hot dog – all‑beef on a poppy‑seed bun “dragged through the garden” (mustard, relish, onion, tomato, pickle, sport peppers, celery salt); never ketchup. Perfect from retro kiosks after a match or gig.

• Deep‑dish pizza – buttery crust layered with mozzarella and bright tomato sauce; a slow, indulgent slice of local history. Settle into classic pizzerias and expect queues.

• Chicago Handshake – a shot of Malört with an Old Style beer; bitter, bracing, and proudly local. Best attempted in laid‑back dive bars with plenty of banter.