22 Things I Wish I'd Known Before My First Trip to Chicago
I've been to Chicago five times now. The first trip, I made every rookie mistake in the book — rented a car (terrible idea), ordered deep-dish pizza three meals in a row (my stomach still hasn't forgiven me), and nearly lost a finger to the January wind because I thought my Brooklyn coat was "warm enough."
Each trip taught me something. Here's everything I've learned, organized by the categories that actually matter.
Getting Around
1. Don't rent a car. I said it once, I'll say it again. The 'L' train covers everything. Blue Line from O'Hare is $5. Day pass is $5 on a Ventra card ($5 card fee). Downtown parking runs $30-60/day. And traffic on the Kennedy Expressway at rush hour is the kind of experience that makes you question your life choices.
2. The Brown Line loop is a free architecture tour. Just ride the full loop through the Downtown elevated tracks. You'll pass the Merchandise Mart, the Board of Trade, and Marina City (those corncob towers) from a perspective you can't get on the ground. Takes 30 minutes. Best on a clear afternoon.
3. Get the Ventra app, not the physical card. Tap your phone to pay on the 'L' and buses. It's faster and you won't lose the card in your hotel room. Works with Apple Pay and Google Pay too — just tap a credit card for $2.50/ride.
4. Uber from Midway is sometimes cheaper than the 'L.' If you're traveling with 2+ people, a rideshare from Midway airport to Downtown ($15-20 split) can be faster and comparable in cost to the Orange Line ($5 each).
Food & Drink
5. Order tavern-style thin-crust if you want locals to respect you. I covered this above but it bears repeating. Deep-dish once. Thin-crust cut in squares the rest of the time. Pat's Pizza on Lincoln Ave. You're welcome.
6. The Italian beef sandwich is the real signature food. Portillo's on West Ontario ($8-10). Order it "dipped" (the bread soaked in gravy) with hot giardiniera (spicy pickled vegetables). Have napkins ready. This is not a clean-eating situation.
7. Garrett Popcorn's "Chicago Mix" is a legitimate souvenir. Cheese and caramel popcorn mixed together ($10-15 a bag). It sounds wrong. It's incredibly right. Multiple locations on Michigan Avenue. Your family will be impressed and confused simultaneously.
8. Skip Navy Pier restaurants. All of them. Walk 15 minutes to River North instead. Even the chains are better off-pier. The Ferris wheel and summer fireworks are the only reasons to visit.
9. The West Loop is Chicago's restaurant capital. Randolph Street between Halsted and Racine is where the city's best chefs opened their restaurants. Girl & The Goat ($18-38 per dish, book weeks ahead), Au Cheval ($16 burger, 2-hour wait), and Publican ($15-30, beer-hall vibes) are all within walking distance.
10. Deep-dish takes 40+ minutes. Plan accordingly. These pizzas are baked to order. Don't show up starving. Have a drink. Breathe. The wait is part of the ritual.
Sightseeing
11. Millennium Park before 9AM is a different place. The Bean (Cloud Gate) with nobody around it, reflecting the skyline in peace. Crown Fountain actually visible. The Lurie Garden quiet. By 10AM it's packed. By noon it's a selfie factory. Early morning is yours.
12. 360 Chicago (John Hancock) beats the Skydeck for sunset. The Willis Tower Skydeck ($30, 103rd floor) has The Ledge glass boxes. But 360 Chicago at the Hancock Center ($30) faces west over the lake and city, which is exactly where you want to be looking at sunset. Better yet — skip both and go to the Signature Lounge on the 96th floor. Same view. Free with a drink purchase ($18-22 cocktails).
13. The architecture river cruise is the single best tourist activity in Chicago. Chicago Architecture Center, $49, 90 minutes, book at architecture.org. It sells out in summer. I've done it three times and learned something new each time. There's a reason this city is called the birthplace of the modern skyscraper.
14. Lincoln Park Zoo is free and actually great. Not "great for a free zoo" — actually great. Open daily 10AM-5PM. The Great Ape House and Farm-in-the-Zoo are highlights. And the surrounding Lincoln Park neighborhood has excellent dining.
Weather & Packing
15. Check the forecast. Then pack warmer. Whatever you think Chicago weather is, add 10 degrees of cold and 20 km/h of wind. The lake effect is real. Even in September, evenings along the lakefront can drop to 10°C.
16. Summer is glorious and worth scheduling around. June through September, Chicago transforms. Free outdoor concerts at Pritzker Pavilion. Beaches along the lakefront. Rooftop bars everywhere. Average temperatures 25-30°C. It's one of the best summer cities in America.
17. January-February requires survival gear. Thermal base layer. Fleece mid-layer. Windproof outer shell. Insulated waterproof boots. Serious gloves. A hat that covers your ears. I'm not being dramatic — wind chill regularly hits -25°C, and "The Hawk" (the wind off Lake Michigan) will find every gap in your clothing.
18. Learn about the Pedway. 40 blocks of underground tunnels connecting Downtown buildings. In winter, you can walk from the 'L' to your hotel to the Art Institute without going outside. Maps are posted at entrances, but it's confusing at first — just follow the signs.
Culture & Etiquette
19. CityPASS saves real money if you're doing 3+ attractions. $98 covers Skydeck, Shedd Aquarium, Field Museum, and two more attractions. That's about 50% off individual tickets. If you're museum-hopping, it's a no-brainer.
20. Tip 18-20% at restaurants. This is non-negotiable in Chicago. The standard is the same as the rest of the US. Bartenders: $1-2 per drink. Uber/Lyft: 15-20%.
21. Don't be afraid of the 'L' at night. The Blue, Brown, and Red Lines through tourist areas are safe and well-monitored late into the evening. Standard city awareness applies — keep your phone in your pocket, stay alert — but Chicago's public transit is not the danger zone some people imagine.
22. Talk to people. This is the biggest one. Chicagoans are absurdly friendly. Not performatively friendly like some cities. Genuinely, sincerely friendly. Ask your bartender what neighborhood they live in. Ask the person next to you at the blues club what they're drinking. Chicago is a city that rewards conversation.
I went the first time on a work trip. Stayed three extra days. Went back four more times. The sixth trip is already on the calendar.
If you're planning a US music and food tour, pair Chicago with New Orleans for jazz and blues, or head north to Toronto for a different kind of multicultural food city.
Pack the warm coat. Skip the car. Order the Italian beef dipped. You'll figure out the rest.
