America's Most Underrated City
Chicago is the city that NYC residents don't want you to discover. It has world-class architecture (arguably the best in America), a legendary food scene, incredible live music (blues, jazz, hip-hop), professional sports teams that inspire genuine devotion, and a massive freshwater lake that looks like the ocean.
It's also significantly more affordable than New York or San Francisco, friendlier, cleaner, and easier to navigate. The "L" train system works. The neighbourhoods have genuine character. The skyline — especially viewed from Lake Michigan — rivals Manhattan.
For UK visitors, Chicago is a revelation. If you've "done" New York and LA, Chicago is where the real discovery begins.
The Must-Do Experiences
Architecture River Cruise
Board a boat on the Chicago River and spend 90 minutes learning about the city's extraordinary architecture — Frank Lloyd Wright, Mies van der Rohe, the Tribune Tower, Marina City (the "corn cob" buildings). This is consistently rated the #1 visitor experience in Chicago. £30-40. Book in advance.
Deep-Dish Pizza
This is not pizza as you know it. It's a 2-inch-deep pie with a buttery crust, layered with cheese and chunky tomato sauce on top. Lou Malnati's and Giordano's are the classics. Pequod's has a caramelised cheese crust that's considered the best by locals. Order one, share it, and allow 40 minutes for it to arrive (they bake fresh).
Millennium Park & "The Bean"
Cloud Gate (universally called "The Bean") is a 33-foot mirrored sculpture that reflects the Chicago skyline. It's bizarre, joyful, and completely free. The surrounding Millennium Park has Frank Gehry's Pritzker Pavilion (outdoor concerts in summer), Lurie Garden, and Crown Fountain. Free.
The Art Institute of Chicago
One of the oldest and largest art museums in the United States. The collection includes Monet, Renoir, Seurat's "A Sunday Afternoon," Edward Hopper's "Nighthawks," and Grant Wood's "American Gothic." Allow 3-4 hours minimum. £20-25.
Blues and Jazz Clubs
Chicago is the birthplace of electric blues. Buddy Guy's Legends (founded by the living legend himself), Kingston Mines (two stages, music until 4am), and Green Mill (jazz, a former Al Capone speakeasy). Cover charges £5-15. This is authentic, world-class live music.
Wrigley Field / Cubs Baseball
One of America's oldest and most beautiful ballparks (1914). The ivy-covered outfield walls, the manual scoreboard, the Wrigleyville neighbourhood of bars surrounding it. Even if you don't understand baseball, this is an essential American experience. Tickets from £15.
Lake Michigan Beaches
Chicago has 26 miles of lakefront. North Avenue Beach and Oak Street Beach have downtown skyline views. In summer (June-September), the beaches are packed and the water is swimmable. It looks like the sea. Free.
Food & Drink
- Deep-dish pizza — Lou Malnati's, Giordano's, Pequod's. See above.
- Chicago-style hot dog — Vienna beef frank, yellow mustard, green relish, onion, tomato, pickle spear, sport peppers, celery salt, poppy seed bun. Never ketchup. Portillo's or Superdawg.
- Italian beef sandwich — Thinly sliced, slow-roasted beef on Italian bread, dipped in au jus (the pork drippings gravy). Al's #1 Italian Beef or Mr. Beef. Order it "dipped" (the whole sandwich dunked in gravy). £8-10.
- Craft beer — Chicago has an incredible craft scene. Revolution Brewing, Half Acre, Goose Island taproom (the original, not the macro version).
Budget Snapshot
| Item | Approximate Cost (GBP) |
|---|---|
| Heathrow → ORD (return) | £350-700 |
| Mid-range hotel (per night) | £100-180 |
| Architecture river cruise | £30-40 |
| Deep-dish pizza (to share) | £20-30 |
| Cubs game ticket | £15-60 |
| Blues club cover | £5-15 |
| Week total (budget) | £1,000-1,500 |
| Week total (comfortable) | £1,800-3,000 |
Insider Tips
- Winter is brutal. November–March, Chicago earns its nickname "The Windy City." Wind chill can hit -20°C. Visit May–October for the best experience.
- The "L" train is excellent. Buy a Ventra card. The Blue Line runs directly to/from O'Hare Airport. No expensive airport transfer needed.
- Explore the neighbourhoods. Pilsen (Mexican art and food), Wicker Park (indie shops and bars), Logan Square (craft cocktails), Hyde Park (University of Chicago, Obama's old neighbourhood).
- Summer in Chicago is magic. Festivals, outdoor concerts at Millennium Park, beach days, rooftop bars. Chicago in summer is one of the best cities in America.
- Tip on everything. Same as everywhere in the US: 18-20% at restaurants, $1-2 per drink at bars, $2-5 for hotel bellhops.