Quick Answer: Chicago is easy to reach by plane (O’Hare or Midway), train (Amtrak to Union Station), or car. Once here, you don’t need a car—the CTA train and buses go everywhere, and downtown is very walkable. Plan to stay in River North or Streeterville for the best first-timer experience. Budget $150–$300/night for a good hotel, and give yourself at least 3–4 days to see the highlights.
Thinking about planning a trip to Chicago? Whether it’s your first time or a return visit, the Windy City can feel overwhelming with so much to see and do. As someone who once explored Chicago as a visitor and now navigates it like a local, I’ve learned the best ways to get here, get around, and find the perfect place to stay.
This guide covers the practical stuff: transportation options, how to get from the airports and train station to downtown, getting around the city, and hotel recommendations for every budget—plus insider tips to help you make the most of your trip.
Looking for what to actually do once you get here? Check out my First-Time Visitor’s Guide to Chicago for must-see experiences, neighborhood exploration, and simple itineraries.
Let’s get you here.
📋 In This Guide
✈️ How to Get to Chicago
Chicago is one of the most accessible cities in the country—major hub for flights, Amtrak’s busiest station, and easy highway access from anywhere in the Midwest. Here are your options:
Flying In: O’Hare vs. Midway
Chicago has two airports, and which one you fly into matters more than you’d think.
O’Hare International Airport (ORD) — 📍 10000 W O’Hare Ave
- One of the busiest airports in the world—more flight options, but also more chaos
- CTA Blue Line runs directly downtown (45 minutes, $5)
- Uber/Lyft to downtown: $35–$60 depending on traffic
- Best for: More flight choices, international connections
Midway International Airport (MDW) — 📍 5700 S Cicero Ave
- Smaller, easier to navigate, often cheaper flights (Southwest hub)
- CTA Orange Line runs directly downtown (30 minutes, $2.50)
- Uber/Lyft to downtown: $25–$45
- Best for: Budget airlines, less stressful experience
💡 Pro Tip: If you’re taking a rideshare from either airport, follow signs to the designated pickup zones—they’re separate from taxi stands and clearly marked in the app.
🚆 Arriving by Train (Amtrak)
If you’re coming from the Midwest or don’t mind a longer ride, Amtrak is a genuinely pleasant way to arrive. Chicago’s Union Station (📍 225 S Canal St) is the main hub, with routes from New York, Washington D.C., St. Louis, Milwaukee, and dozens of other cities.
Union Station is big but well-marked. After you get off, follow signs to the Great Hall or street exits. The closest CTA stops are Clinton (Blue Line) and Quincy (Brown, Orange, Pink Lines)—both a short walk. Taxis and rideshares are available right outside.
🚌 Arriving by Bus
Taking Greyhound, Megabus, or FlixBus is the most affordable way to get here if you’re coming from nearby cities.
- Greyhound Station: 📍 630 W Harrison St (near Union Station, easy CTA access)
- Megabus & FlixBus: Drop-off locations vary—usually near the Loop or West Loop. Check your ticket for the exact spot.
💡 Pro Tip: Megabus and FlixBus are usually cheaper and more comfortable than Greyhound. Book in advance for the best fares.
🚗 Driving to Chicago
You can definitely drive here, but here’s the honest truth: you probably don’t need your car once you arrive. Parking is expensive, traffic is frustrating, and public transit/walking will get you everywhere you want to go.
If you do drive:
- Major highways: I-90/I-94 (Kennedy/Dan Ryan), I-290 (Eisenhower), I-55 (Stevenson)
- Tolls: Expect $5–$10 depending on your route. Get an I-PASS or E-ZPass, or pay online within 14 days.
- Hotel parking: $50–$80/night for valet (yes, really)
- Garage parking: $30–$50/day downtown. Apps like SpotHero let you book in advance at a discount.
💡 Pro Tip: If you’re driving in but don’t need the car for sightseeing, park outside the city and take the CTA train in. Many suburban stations have free or cheap parking, and it’s way less stressful.
🚇 Getting Around Chicago
Chicago is very manageable without a car. Downtown is walkable, and the CTA (Chicago Transit Authority) will get you everywhere else. Here’s what you need to know:
The “L” Train
Chicago’s elevated train system (we call it “the L”) has 8 color-coded lines running through the city. The ones you’ll likely use most:
- Blue Line: O’Hare ↔ Downtown ↔ Wicker Park/Logan Square
- Red Line: North Side ↔ Downtown ↔ South Side (runs 24/7)
- Brown Line: Loop ↔ Lincoln Park ↔ North Side neighborhoods
- Orange Line: Midway Airport ↔ Downtown
Fares are $2.50 per ride with a Ventra card (you can buy one at any station). Transfers within 2 hours are $0.25.
For a deeper dive, check out my Complete Guide to the Chicago CTA.
Buses
CTA buses fill in the gaps where the L doesn’t go. Same Ventra card, same fare. Google Maps will tell you exactly which bus to take.
Walking
Downtown Chicago is extremely walkable. The Loop, River North, Streeterville, and the Magnificent Mile are all close together—you can easily walk between them. Comfortable shoes are your best friend.
Rideshare (Uber/Lyft)
Widely available and useful for late nights or getting to neighborhoods farther out. Expect $15–$30 for most trips within the city.
🏙️ Best Neighborhoods to Stay In
One of the things that really cemented my love for the city of Chicago is its neighborhoods. This is a city built for people, and each neighborhood has its own character. Where you stay matters—here’s what you need to know:
River North
This is my #1 pick for first-time visitors. You’re centrally located to great shops and restaurants, with easy public transportation to other parts of the city. It’s within walking distance to the stunning Lake Michigan shoreline and the world-famous Chicago Riverwalk. Also home to Chicago’s famous deep-dish pizza spots like Lou Malnati’s and Gino’s East.
Streeterville
A waterfront neighborhood near Navy Pier and the Magnificent Mile. Great for families who want lakefront views. Like River North, Streeterville is convenient for dining, shopping, and accessing public transportation—you’ll have a wide variety of Streeterville restaurants within steps. The Museum of Contemporary Art is a neighborhood highlight.
The Loop & Downtown
The heart of the city, home to Millennium Park, The Art Institute, and historic skyscrapers. Don’t miss the shops on State Street, including the iconic Marshall Field’s building (now Macy’s). Great for anyone who wants to be within walking distance of major attractions—just note it gets quiet at night.
Want to explore beyond downtown? Check out my First-Time Visitor’s Guide for neighborhood recommendations like Wicker Park, Logan Square, and Pilsen.
🏨 Where to Stay: Hotel Recommendations
Finding the right place to stay in Chicago depends on your budget and preferred location. Here are some of my favorite hotels in different price ranges:
Luxury ($300+)
- The Langham Chicago — 📍 330 N Wabash Ave. Five-star riverfront hotel with stunning views and an award-winning spa.
- Pendry Chicago — 📍 230 N Michigan Ave. Stylish boutique hotel in a historic Art Deco building, steps from Millennium Park.
Mid-Range ($150–$300)
- Hotel EMC2 — 📍 228 E Ontario St. Trendy Streeterville hotel with a fun science-meets-art theme.
- Chicago Athletic Association — 📍 12 S Michigan Ave. Historic hotel with a speakeasy bar and rooftop views of Millennium Park.
- The Talbott — 📍 20 E Delaware Pl. Sophisticated Gold Coast gem with a European-inspired vibe.
Budget ($100–$150)
- Hampton Inn Chicago Downtown West Loop — 📍 116 N Jefferson St. Modern, budget-friendly, free breakfast, rooftop patio.
- Club Quarters Hotel Wacker at Michigan — 📍 75 E Wacker Dr. No-frills but clean, right on the river, great location for the price.
💰 What to Expect Cost-Wise
Chicago isn’t the cheapest city, but it’s more affordable than New York or San Francisco. Here’s a rough breakdown:
| Expense | Budget | Mid-Range | Splurge |
|---|---|---|---|
| Hotel (per night) | $100–$150 | $150–$300 | $300+ |
| Meals (per day) | $30–$50 | $50–$100 | $100+ |
| Transit (per day) | $5–$10 | $10–$20 | $30+ (rideshares) |
| Attractions (per day) | $0–$25 | $25–$50 | $50+ |
Bottom line: A comfortable mid-range trip runs about $200–$350/day per person (including hotel split with a partner). Budget travelers can do it for $100–$150/day if you’re strategic.
📅 When to Book & How Many Days You Need
How far in advance to book:
- Flights: 4–8 weeks out for best prices
- Hotels: 2–4 weeks out (earlier for summer or major events)
- Restaurants (popular ones): 1–2 weeks for reservations
- Architecture boat tours: Book a few days ahead in summer—they sell out
How many days you need:
- 2 days: Enough for the highlights (Millennium Park, architecture cruise, one museum, deep-dish pizza)
- 3–4 days: Ideal for first-timers—see the main attractions plus explore a neighborhood or two
- 5+ days: Time to go deeper—day trips, multiple neighborhoods, slower pace
Ready to Plan Your Chicago Trip
Planning a trip to Chicago doesn’t have to be overwhelming. With multiple transportation options, diverse neighborhoods, and accommodations for every budget, you’ll find a way to make your visit smooth and stress-free.
Now for the fun part: check out my First-Time Visitor’s Guide to Chicago to figure out what to actually do while you’re here—must-see experiences, neighborhood exploration, common mistakes to avoid, and simple itineraries.
Questions? Please use the comment section below to reach out—I’m happy to help!