I remember when I visited Chicago for the first time and was stressing about where to stay. I did research for weeks, reading hundreds of reviews. Yes, I can get kind of obsessed. But I couldn’t be happier with the hotel I chose.
So I knew I had to put together this guide, so you can choose the right area to stay in for Chicago for your needs and interests. All neighborhoods in Chicago offer distinct flavors and tastes of Chicago life.
Whether you are staying for a long trip or a quick Midwest weekend getaway, these are the top areas and neighborhoods to stay in Chicago!
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Article overview
Best areas to stay in Chicago
Where you choose to stay in Chicago should depend on the sights you want to see and how much time you have. If you only have a weekend in the city, I recommend staying Downtown in areas such as the Loop and River North.
I am so happy that I chose to stay at the Pendry Chicago, even though it cost a little more than I normally would spend. It is a gilded Art Deco dream!
However, if you have a week, I recommend staying a little further out in a laid-back and less touristy area like Wicker Park or Logan Square, where accommodation is cheaper. Wicker Park is my favorite area once you get the main attractions out of the way.
Below I have included a map outlining the best areas and neighborhoods to stay in Chicago if it’s your first time in the city.
1. The Loop
🌟 Best area for first-time visitors/short stays | 🏨 Best hotels: Pendry Chicago • citizenM Chicago Downtown | 🎫 Best tours: Gangsters and Ghosts Walking Tour • Chicago Walking Food Tour
The main area of Downtown Chicago, often referred to as the Loop, is the top destination for first-timers seeking the quintessential Chicago experience. This area is renowned for its proximity to some of the city’s top attractions, making it an ideal base.
Staying downtown means you’re just a short walk or a quick L (elevated train) ride away from the iconic Millennium Park, where you can snap a selfie with the reflective Cloud Gate sculpture, affectionately known as “The Bean.” The perfect place to get some shots to go with these Chicago Instagram captions.
This is also where the Historic Route 66 sign is located, a perfect leaping-off point for many Midwest road trips.
✅ Pros of the Loop area
- Most central location
- Walkable
- Many top attractions
- Close to shops, bars and restaurants
- All the trains meet here
❌ Cons of the Loop area
- Lots of people and noise
- Expensive
- Geared towards tourists
2. Magnificent Mile
🌟 Best area for shopping and nightlife/short stays | 🏨 Best hotel: Omni Chicago Hotel | 🎫 Best tour: Chicago Architectural River Cruise
The Magnificent Mile, often referred to as The Mag Mile, is one of Chicago’s premier commercial districts, renowned for its luxury retailers, high-end boutiques, large department stores and posh hotels.
Stretching along Michigan Avenue from the Chicago River to Oak Street in the Near North Side, this iconic boulevard offers more than just shopping; it’s an essential Chicago experience that combines retail, dining, and entertainment with stunning urban architecture.
✅ Magnificent Mile pros
- Great for shopping
- Central location
- Easily walkable
- Many well-known landmarks
- Great for nightlife
- Start of architectural river cruise
❌ Magnificent Mile cons
- One of the most expensive areas
- Can feel touristy
3. River North
🌟 Best area for nightlife/short stays | 🏨 Best hotels: Moxy Chicago Downtown • The Gwen | 🎫 Best tour: Chicago Pizza Walking Tour & Tasting
Just north of the Loop, River North is known for its art galleries, nightlife, and upscale dining. It’s a trendy area with a lot of foot traffic and a high concentration of hotels, making it a safe and convenient location for visitors.
River North comes alive at night with its many bars, nightclubs, and lounges. It’s a great place to experience Chicago’s lively evening scene, with options for live music, craft cocktails, and dancing. I especially recommend River North to young professionals who want that vibrant city life feel.
✅ pros of River North
- Central location
- Many shops, bars and restaurants
- Walkable
- Vibrant nightlife
- Majestic architecture
❌ cons of River North
- Lacks charm
- Can be noisy
- One of the more expensive areas
4. Wicker Park
🌟 Best area for young people/hip vibes | 🏨 Best hotels: Wicker Park Inn • The Robey | 🎫 Best tours: Historic Homes Wicker Park Walking Tour
Wicker Park is the best area to stay in Chicago for anyone wanting to experience the city beyond the typical tourist spots.
Renowned for its artistic atmosphere, you can explore numerous art galleries, or catch live music and performances at local venues. The streets are lined with an eclectic mix of vintage stores and boutiques, perfect for those hunting for unique finds.
Foodies will love the variety of dining options, from cozy coffee shops to Instagrammable restaurants. Getting around Wicker Park is a breeze, with its well-connected bus lines and the accessibility of the Blue Line train.
✅ Wicker Park pros
- Hip vibe
- Colorful murals
- Instagrammable cafés and restaurants
- A mix of tourists and locals
- Hike and bike on the 606
❌ Wicker Park cons
- Can be a bit noisy
- Not within walking distance of main attractions
5. West Loop
🌟 Best area for foodies | 🏨 Best hotels: The Hoxton Chicago • Sonder Market Hall | 🎫 Best tour: Fulton Market Donut Adventure & Walking Tour
The West Loop, once an industrial warehouse district, has transformed into one of Chicago’s most dynamic and stylish areas, making it a top pick for tourists seeking both comfort and adventure in the city.
Renowned for its culinary scene, you can indulge in some of the city’s best dining experiences, ranging from Michelin-starred restaurants to casual, trendy eateries, ensuring every meal is memorable.
The area’s proximity to the Loop means tourists can easily access the main attractions through a short ride on the Green or Pink Line trains.
✅ West Loop pros
- Heaven for foodies
- Trendy, industrial vibe
- Lively
❌ West Loop cons
- Limited accommodation options
- Further from the main attractions
6. Gold Coast
🌟 Best area for luxury | 🏨 Best hotels: Ambassador Chicago • Viceroy Chicago | 🎫 Best tours: Lakefront Neighborhoods Bike Tour • Echoes of Elegance Architectural Splendors
Gold Coast is an affluent and historic neighborhood located just north of downtown Chicago, within walking distance of the Magnificent Mile. I love this neighborhood for its historic mansions and vintage row houses, many of which date back to the late 19th and early 20th centuries.
Gold Coast is also home to a variety of high-end boutiques, designer stores, and luxury brands, particularly along Oak Street, which is often considered the Rodeo Drive of the Midwest.
✅ Gold Coast pros
- Luxurious atmosphere
- Quiet and safe
- Centrally located, walkable
- Close to beaches and Lincoln Park
❌ Gold Coast cons
- Expensive
7. Old Town
🌟 Best area for history buffs | 🏨 Best hotel: The Sono Chicago | 🎫 Best tour: Oldtown Triangle Architecture Walking Tour
Old Town attracts tourists with its captivating blend of historical significance and contemporary flair, making it one of the best areas to stay in Chicago.
History buffs can enjoy guided architectural tours, shedding light on Old Town’s rich past and its significance in Chicago’s development. The “Old Town Triangle” is the only spot that survived the Great Chicago Fire in 1871.
This neighborhood offers an array of activities, from exploring the famed Second City comedy club, where many legendary comedians have honed their craft, to leisurely strolls through the picturesque streets lined with Victorian-era buildings.
✅ Old Town pros
- Perfect for foodies
- Victorian area architecture
- Many historic attractions
- See famous comedy acts
❌ Old Town cons
- Far from the main attractions downtown
- Fewer hotel options
- Not the best nightlife
8. Logan Square
🌟 Best area for a laid-back local experience/longer stays | 🏨 Best accommodation: Logan Square Modern Apartment | 🎫 Best experience: Fortune Reading with Cheese (yes really)
Logan Square, one of the Chicagos’s oldest and most iconic neighborhoods, is home to local creatives and musicians, as well as excellent shops and eateries. It is also a great area for families.
This neighborhood offers a variety of things to do, from meandering through the Logan Square Farmers Market to enjoying the latest indie films at the Logan Theatre. Also go for a walk on the Bloomingdale Trail, once part of the L train network.
You can explore the iconic Illinois Centennial Monument for a touch of history or indulge in a meal at one of the cutting-edge restaurants that have set up shop in beautifully restored buildings.
✅ Lakeview pros
- Hip and creative
- Great restaurants
- Beautiful architecture
❌ Lakeview cons
- Farther from the city center
9. Lakeview
🌟 Best area for baseball fans/longer stays | 🏨 Best hotels: Hotel Zachary • Lakeview 2-bed apartment | 🎫 Best tour: Chicago Cubs Baseball Game
Lakeview, set on the shores of Lake Michigan, is a residential neighborhood. It’s a great place to stay if you want to experience a more local side of Chicago or for returning visitors.
Its crown jewel, Wrigley Field, offers baseball fans a chance to catch a Cubs game in one of the oldest ballparks in America. And, trust me, experiencing a game is fun even if you’re not into baseball at all.
The neighborhood’s extensive lakefront paths provide the perfect setting for biking, jogging, or simply enjoying breathtaking views of the Chicago skyline.
✅ Lakeview pros
- Quiet and safe residential area
- Wrigley Field
- Beautiful Lake Michigan waterfront
- One of the easier places to drive by yourself
❌ Lakeview cons
- Farthest from the city center of the areas I recommend
Quick Chicago travel guide
Here’s a quick overview of the best times to visit Chicago and how to get around the city.
What is the best time to visit Chicago?
The best time to visit Chicago is generally considered to be between April and October when the weather is warm and the city offers a plethora of festivals and outdoor activities. My personal favorite time to visit Chicago is late April and early October.
The peak tourist season is during the summer months, from June to August. This is the ideal time to enjoy the beaches along Lake Michigan, and attend events like Taste of Chicago and the Chicago Air and Water Show.
However, if you prefer fewer crowds and potentially lower accommodation rates, the shoulder seasons of spring (April and May) and fall (September and October) are excellent choices.
Winter in Chicago, from November to March, can be quite cold and snowy, which deters some visitors. But if you don’t mind bundling up, you can enjoy the city’s winter charm, holiday lights, and festivities, including the Christkindlmarket, ice skating rinks, and potentially better deals on hotels.
How to get around Chicago
Getting around Chicago using public transportation is convenient and efficient due to the city’s extensive network of buses, trains, and shared bike programs such as Divvy Bikes.
The Chicago Transit Authority (CTA) operates the two main modes of public transit: buses and the ‘L’ (short for “elevated”) train system. Train and bus lines are laid out like a grid, with 8 train lines and 129 bus routes. All the train lines meet downtown to form a loop.
📲 Pro tip >> Download the Ventra app or get a Ventra Card from one of the many convenience stores and stations that sell them.
If you plan on staying in the downtown neighborhoods of Chicago, you should be able to walk to most attractions as the city is mostly flat. Rideshares, Uber, Lyft, and ´taxi services like “Curb”, are also largely available throughout the city.
Chicago also has scenic walking paths such as the Lakefront Trail along Lake Michigan and the Riverwalk on the Chicago River, as well as beautiful parks like Grant Park, Millennium Park, and Lincoln Park.
🚁 Looking for a unique experience? The best thing you can do in Chicago is to take a private Skyline Helicopter Tour. Ideal for special occasions, this tour accommodates up to three people. It is so much fun and an experience you will remember forever!
How to get to the city center from Chicago airport
Public transport: If you’re coming from Chicago O’Hare International Airport, the blue line connects you to downtown. If you’re flying into Midway Airport, the orange line will bring you downtown.
Rideshare: You can take an Uber or Lyft from the airport, but you will need to transfer to the Terminal 2 departures area using the Airport Transit System, which takes approximately five minutes.
Direct transfer: After traveling for 15+ hours from Europe, or if I’m arriving at night, all I want is to step into a waiting car and be taken straight to my hotel. The driver below is the most affordable direct transfer I’ve found with one price for up to 3 persons.
Final thoughts: Where to stay in Chicago
For first-time visitors to Chicago, staying in Downtown Chicago connects both top city attractions and top locations in the region like Indiana for some of the best Midwest hiking.
As mentioned Wicker Park is my personal favorite because of the creative atmosphere, while Logan Square presents a blend of historic charm and contemporary energy, with its bustling farmer’s markets and indie film theaters.
Old Town offers a peek into Chicago’s rich history with its architectural tours and serene parks, along with a vibrant nightlife and arts scene. Gold Coast is there if you prefer a more luxurious stay.
For my fellow foodies, West Loop is a great choice with easy access to the main attractions. If you’re in town for a longer stay or a baseball game at Wrigley Field, you can’t go wrong with Lakeview.
🌟 Visiting Chicago on a weekend? >> Check out my ultimate Chicago weekend itinerary.
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