9 BEST areas to stay in Chicago for first-timers + map

Are you looking for the best areas to stay in Chicago? I get it, there are so many great options that it’s difficult to choose just one. And that’s why I put together this guide, so you can choose the right area to stay in for Chicago for you! 

All neighborhoods in Chicago offer distinct flavors and tastes of Chicago life. For first-time visitors, the question of where to stay in Chicago to experience the best of the city is paramount.

My top recommended neighborhoods are Downtown and Wicker Park, but let’s take a closer look. 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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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.

Downtown Chicago, the heartbeat of the city, is an ideal choice for those eager to be steps away from towering skyscrapers, the reflective “Bean” sculpture in Millennium Park, and an array of world-class museums and restaurants.

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 can be a little cheaper.

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.”

Art enthusiasts will appreciate the Art Institute of Chicago, one of the oldest and largest art museums in the United States, located on the edge of Millennium Park. This is also where the Historic Route 66 sign is located, a perfect leaping-off point for many Midwest road trips.  

For a stunning panoramic view of the city and Lake Michigan, Willis Tower (formally known as the Sears Tower) and its Skydeck is a mere walk or L ride away. The Chicago Riverwalk, one of the best things to do in Chicago, runs along the river to the north of the neighborhood.

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.

The area is dotted with impressive buildings and landmarks, such as the historic Water Tower, the John Hancock Center and the Wrigley Building.

DuSable Bridge connects the Magnificent Mile with the Loop and right next to it is the meeting point for the architectural river cruise I highly recommend you experience while in Chicago.

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.

River North boasts the highest concentration of art galleries in the United States outside of Manhattan. The area is also home to the Merchandise Mart, a landmark building with showrooms, offices, and theMART, which hosts design and art events.

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 • Bucktown-Wicker Park Pizza Crawl

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.

Plus, the 606, an elevated park and trail system, provides a scenic route for walking or biking, connecting Wicker Park to other nearby neighborhoods, ensuring a comprehensive exploration of what this unique part of Chicago has to offer.

It’s a somewhat off-the-beaten-path location with tons of things to do, which is why it is one of my favorite neighborhoods. The perfect place to get some shots to go with these Chicago Instagram captions.

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.

Art enthusiasts will appreciate the neighborhood’s vibrant arts scene, with numerous galleries and studios dotting the streets, offering a glimpse into the local culture and creativity.

For those interested in shopping, the West Loop boasts a selection of unique boutiques and designer stores, easily accessible on foot or by bike.

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. The neighborhood is characterized by 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.

In the evening, head to Rush Street and mingle with the city’s trendy crowd at lively bars. And when you’re hungry, check out Velvet Taco, Hugo’s Frog Bar & Fish House and the stunning 3 Arts Club Café.

Its location, within walking distance of the Magnificent Mile, Old Town and River North, makes it the perfect area to stay for sightseeing. You also have the beautiful Oak Street Beach and Lincoln Park lining the east and north sides of the neighborhood.

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.

If you’re a foodie like me, you’ll love the diverse culinary scene, ranging from classic Chicago eateries to trendy restaurants. Check out Old Town Ale House, a rowdy dive bar famous for its wall art, and Frank Sinatra’s favorite and former speakeasy, Twin Anchors.

Thanks to the efficient public transportation system, getting to these activities is a breeze; most attractions are within walking distance, or a short bus or Brown Line train ride away.

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 city’s oldest and most iconic neighborhoods in Chicago, 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 rich 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 the culinary delights at any of the cutting-edge restaurants that have set up shop in beautifully restored buildings.

For those interested in Chicago’s bustling nightlife, Logan Square boasts an eclectic mix of bars and live music venues that cater to all tastes.

Getting around is hassle-free, with many attractions located within walking distance of each other. The area is well-serviced by public transportation, with the Blue Line train providing easy access to other parts of the city.

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. While dining options, ranging from cozy diners to sophisticated gastro-pubs, cater to every palate.

Additionally, Lakeview’s thriving theatre scene, including the famous Briar Street Theater and Music Box Theatre, offers you a taste of Chicago’s fun performing arts culture.

Getting around Lakeview is a breeze with multiple CTA bus routes and the Red Line train offering convenient access to the area’s top attractions. It is also one of the only areas I feel comfortable driving.

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 when you can expect the warmest temperatures and a vibrant atmosphere throughout the city. This is the ideal time for sightseeing, enjoying the beaches along Lake Michigan, and attending 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. The weather is still pleasant, though more variable and the parks are particularly beautiful with spring blooms or autumn foliage.

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: Best areas 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.

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