best neighborhoods to stay in Chicago

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Planning a trip to Chicago? Wondering where you should stay? Anywhere downtown (aka the Loop, the central business district) is usually where most visitors stay, and for good reason. There are many things to do and fabulous restaurants and shops. You’ll be close to the lakefront and downtown attractions like the Museum Campus, Buckingham Fountain, Navy Pier & Millennium Park. You can’t go wrong staying anywhere from the Gold Coast (near northside) to the South Loop and anywhere in between. But if you want to live like a local or are traveling with your kids or a larger group, you should consider staying in a neighborhood. This post is a quick guide to the best neighborhoods to stay in Chicago to help you plan your trip.

The Gold Coast, Old Town, Lakeview, Wicker Park, and South Loop are all good neighborhoods to stay in when visiting Chicago. All are walkable to cafes, restaurants, bars & shops with easy access to downtown by a quick ‘L’ or bus ride, taxi, or rideshare.

1/Gold Coast

Surprising what used to be swampy marshland & cemeteries now have some of Chicago’s most exclusive, historic homes. The Gold Coast is located In a pocket just north of the Magnificent Mile, west of the lake (Lake Michigan), and south of Lincoln Park. Wander through this fancy neighborhood and admire the elegant Charnely-Persky house by Frank Lloyd Wright (click here for info to take a tour) and an array of gorgeous mansions owned by influential Chicagoans, from architects to newspaper magnates to social reformers.

Walk down Historic Astor Street from the Cardinal’s House (taking a peek behind the coach house at the wooden alley) to the spectacular Potter Palmer rowhouses. Head over to State Parkway, where the original Playboy Mansion is located, and has since been converted to condos. If the walls could talk!

Keep heading south on State Parkway, and you’ll find Ambassador Chicago. The once-famous Ambassador East Hotel in the 1930s was the place to be & be seen by many Hollywood celebrities. Make your way down Rush Street. Stop somewhere, grab a drink & relax. This is Chicago’s version of Paris. Great people watching. Then, head over to Oak Street, Chicago’s most prestigious shopping street. Once you reach Michigan Avenue, head south to the Historic Water Tower District to check out one of the surviving buildings of the Great Chicago Fire of 1871.

where to stay

I’ve had clients recommend both Ambassador Chicago & The Thompson Hotel. Check here for Expedia’s best rates. Click here to look for a vrbo.

how to get there

You can get to the Gold Coast in many ways. Check the CTA trip planner for multiple train & bus routes.

where to eat/drink

A couple of my favorite places to eat in the Gold Coast are the 3rd Coast Cafe & Velvet Taco. I also like Nico Osteria and the 3 Club Arts Cafe. The 3 Club Arts Cafe resides in the beautiful courtyard of the historic Three Arts Club, once a home for young women in the arts. There are many options for whatever mood you are in and how much time you have.

2/ Old Town

The neighborhood of Old Town is a great neighborhood to stay in because of its proximity to downtown, just west of the Gold Coast, and its many restaurants, pubs & shops. Meander through the neighborhood and admire the late 1800s architecture styles, including worker cottages & fire shanties that date back to the Great Chicago Fire of 1871. Check out St Michael’s church, which was mostly destroyed in the fire but quickly rebuilt. The locals say that know you are in Old Town if you can hear the bells of St. Michael’s. Walk a little north, and you’ll discover a Buddhist Temple.

If you see some funky, artistic work sprinkled throughout the neighborhood, it would be artist Edgar Miller. Old Town has gone through many phases, and today is a vibrant & interesting place to live. North Avenue & Wells Street is the main section of Old Town. Some fun things to do in Old Town: Second City & Zanies.

You are close to the Chicago History Museum. Check out the exhibits or walk through the new Jaffee History Trail just outside of the museum. Look for the giant metal blob, a relic from the Great Chicago Fire that was part of a hardware store, and the Couch Tomb, evidence that this area was once a city cemetery. Lincoln Park Zoo & Conservatory is a quick walk north.

where to stay

Here are a couple of hotels in Old Town, the Hotel Lincoln or the Level Hotel. Or click here if you are looking for a vrbo.

how to get there

You can take the Brown Line ‘L’ train (Sedgwick stop) or the 22, 36, or 156 bus downtown. Check CTA trip planner.

where to eat/drink

Go to Kamehachi, a sushi staple before sushi became popular, Adobe Grill for creative & delicious Mexican food, or go old school and head over to Twin Acres for ribs or Topo Gigio for Italian. Chocolate freak like me? Must go to Cocoa + Co and the Fudge Pot.

3/Wicker Park

Wicker Park was made up of middle-class artisans and working-class Germans, Norwegians, Poles, and Jews who settled here around 1870. In the following decades, wealthy families who were not welcome in the Gold Coast because of their foreign roots built homes here. In the 20th century, the neighborhood declined, and many of the grandest homes were converted to rooming houses. It was not until the 1980s that this area started to gentrify, just as small businesses sprang up along Milwaukee & Damen.

Wicker Park still maintains some of its Old World feel but has a more eclectic, hip vibe today. It does have it all, historic homes, a large artisan community, shops, cafes, and some of the best indie music venues, bars, and restaurants in the city. Wander around the area to discover cool, independent boutiques, vintage stores, and record shops. Done shopping? Go check out the Bloomingdale Trail (aka the 606), an abandoned railway, and explore all 2.7 miles of the multi-use recreational trail & park.

where to stay

Hotels to look into if you want to stay in Wicker Park are the Robey, Wicker Park Inn & Hyatt Place Chicago/Wicker Park. Click here to look for a vrbo.

how to get there

How do you get to Wicker Park from downtown or O’Hare? Easy, jump on the ‘L’ Blue Line train. You can catch it right from O’Hare and take it to the Damen stop. A quick ride east will get you downtown. Get off at either Loop stop like Dearborn or Washington. Check the CTA trip planner for the best route.

where to eat/drink

There are quite a few good places to eat in Wicker Park; here are some to get you started: urbanbelly, Dove’s Luncheonette, Piece Brewery, Mott St, Taxim, and Big Star. Here are more restaurants for you to choose from.

4/Lakeview

I lived in Lakeview a while back and loved being on the lakefront. Everything is at your doorstep: restaurants, bars, cafes & shops. Here are a couple of posts to learn more about a secret garden in this area & more interesting things about Lakeview. I suggest walking around North Pond Cafe, by the Peggy Notebaert Nature Museum, and continuing through beautiful Lincoln Park. As you head south, you will pass Cafe Brauer, Farm in the Zoo, and the South Pond Nature Walk. Look for the Lincoln Park Zoo Board Walk Pavilion.

where to stay

I lived down the street from the quaint Willows Hotel and a little further north, closer to Boystown, the Best Western Plus Hawthorne Terrace Hotel, which is also very cute. Click here to look for a vrbo.

how to get there

Living in East Lakeview, a block from the lake, the bus is the way to get around. There are multiple routes from which to choose: the 151 Sheridan and the 156 LaSalle offer the best scenery by going through Lincoln Park, and the 22 Clark & 36 Broadway will also get you downtown. The Brown Line ‘L’ train is a little west, but if you don’t mind walking, it will get you where you need to go quicker since it’s not in traffic.

where to eat/drink

My favorite restaurants in Lakeview are La Creperie, Half Shell & Mia Francesca’s. I’m thrilled that all three are still here (post-pandemic) & going strong! Relatively new to my group of favorites but just as good, and BYOB is Chilam Balam. Don’t forget to make a reservation!

5/South Loop

I attended Columbia College in the South Loop. Boy, have things changed in this neighborhood. Today, it is one of the fastest-growing areas in the city. As the name says, it’s just south of the Loop (central business district). You are a quick walk to Buckingham Fountain in Grant Park. Click here to learn more about the 95-year-old fountain. You should also wander around the area looking for the colorful murals of the Wabash Arts Corridor. Click here for a guide.

If you happen to stay here and are a fan of photography, go to the Museum Of Contemporary Photography, part of Columbia College. Interested in hearing some jazz? Jazz Showcase is located in Dearborn Station. In the mood for blues, just down the street is Buddy Guy’s Legends.

A little further south in what is known as the Prairie District (the original Gold Coast) is Chicago’s Women’s Parks & Garden, where locals can get a plot and grow flowers, plants & veggies. Keep heading south, and you’ll come to the historic site of Chess Records, Willie Dixon’s Blues Heaven Foundation. Take a tour or attend one of the free concerts this summer.

where to stay

Stay at the historic Blackstone Hotel or Hotel Blake Chicago. Check here for Expedia’s best rates. Click here if you are looking for a vrbo.

how to get there

You can get to the South Loop in many ways. Check the CTA trip planner for multiple train & bus routes.

where to eat/drink

Eleven City diner, Tapas Valencia, the Chicago Firehouse & Flo & Santos are all good restaurants to check out in the South Loop.

As a tour guide for the past 10+ years, I know these areas pretty well. If you are interested in learning more about these neighborhoods go to toursbycitygirl.com and book a tour with me today!

I hope you enjoyed my quick guide to the best neighborhoods to stay in Chicago & it helped you plan your trip. Tip from a local: Rooftops are popping up all over the city so wherever you find yourself, check google maps on your phone for the closest to you. Best to go off-hours to avoid the crowds. Also, check to see if the restaurant you are interested in takes reservations, if so then make one. We still seem to have a worker shortage, especially in the restaurant world so I highly recommend them.

Have fun exploring!