Welcome to the Windy City! Though the city’s gusty weather may not actually sweep you off your feet, you’re sure to fall in love with the culture and lakefront location of this Midwestern metropolis. Chi-Town is one enormous “town,” so you might be wondering where to stay in Chicago, IL to be best positioned for optimal sightseeing – or whatever it is you have planned while you’re here. At Stay Alfred, we’re all about making these decisions as easy as possible, so we’ve put together a guide that spills all the juicy secrets about our favorite places to stay in Chicago, IL.
Whether you’re searching for a primer on where to stay in Chicago downtown or researching the best neighborhoods for families, this guide will offer plenty of good insight. You’ll also find that we’ve set up shop in each of our top four neighborhoods, so you can always find a spacious Chicago Stay Alfred travel apartment with our signature conveniences, like full kitchens and upscale building amenities, within walking distance of great restaurants and things to do.
Put the Second City in the #1 spot on your bucket list
From the Chicago Cubs at Wrigley Field to real bear cubs at the Lincoln Park Zoo to your favorite animal-print accessories from the designer shops on the Magnificent Mile, Chicago has something for everyone. It’s a world-class financial hub, a wonderful place for a family vacation, and even an excellent choice for a romantic city getaway. What’s all this about the West Coast and the East Coast? We think the “best coast” is right here on the shore of Lake Superior.
Where to stay in Chicago on a budget
Like any big city, Chi-Town can be pricey, and there’s certainly no shortage of expensive luxury hotels around here. If you’re visiting Chicago on a budget, a Stay Alfred travel apartment can be the perfect way to save some of your hard-earned dough – so you can spend it on Chicago’s signature dough: deep-dish pizza.
Jokes aside, from Stay Alfred at Park Michigan to Stay Alfred on State Street, every one of our travel apartments features a full kitchen, so you can enjoy affordable home-cooked meals, and essentials like in-unit laundry and fast WiFi that can rack up quite the bill at a traditional hotel. Our properties are also situated in prime locations, so you can save a few bucks on transportation by walking or taking public transit to Chicago’s top attractions.
Characterized by glittering high-rises, upscale boutiques, and a fabulous dining scene, River North is where Chicagoans work hard and play hard. You’ll find the headquarters of international corporations here as well as renowned restaurants and creative cocktail bars. The top attractions, from museums to shopping to theaters, are all within walking distance. It’s also, as you may have guessed, just north of the Chicago River. Pro tip: if you visit during mid-March, the river will be a beautiful emerald color in celebration of St. Patrick’s Day!
Wondering where to stay in Chicago downtown? Here’s your answer, quick and easy: River North.
Neighborhood Highlights: River North
It might be known as the Windy City, but Chicago has lots of beautiful, sunny days too. Stay Alfred on State Street has the ideal place to soak up the rays: an expansive rooftop pool lined with chaise lounges, cabanas, and a grilling station. Sounds lovely – in the summer, at least! During the rest of the year, you’ll have to make do with the sauna, the indoor basketball court, a fitness center, a library, and a lounge with a pool table.
River North for Friends
Raise a glass to your friends getaway in Chi-Town with a drink at one of Chicago’s best cocktail bars, many of which are conveniently located in River North. The tropical Three Dots and a Dash serves up tiki-style cocktails, which are so authentically island-y that if you visit in the middle of winter, you might forget for a second that you’re in the Great White North. It’s not a bad thing until you step outside without your coat! Some other watering holes with an emphasis on mixology include Arbella, Gilt Bar (cozy library vibes), Watershed (nice local beer selection), and The Drifter. If you can find The Drifter, that is. This subterranean speakeasy is hidden behind a shelf stacked with dishes and is absolutely worth looking for.
River North for Business Travelers
Treat your clients or partners to a world-class meal at one of Chicago’s top steakhouses in the River North area. It’s only natural that this office building-filled neighborhood would also be filled with fantastic business-friendly restaurants, so you’ve got plenty of choices. For a really special occasion, book a table at Bavette's Bar & Boeuf, truly the cream of the crop, with “Chicago steakhouses” being the “crop.” With a bit of French influence, this is the kind of place where you don’t need to ask for steak sauce! You may, however, want to book a ticket to Paris tout suite!
Other stellar steakhouses in the area include Kinzie Chophouse, Mastro's Steakhouse (featuring nightly live piano music), and you also have Harry Caray's Italian Steakhouse with its signature Italian twist, so you can have your steak with a side of chicken parmigiana or rigatoni alla vodka. Our recommendation when you dine at any of these hotspots: wear your fanciest elastic-waist pants.
River North for Families
The River North neighborhood is surely the neighborhood you’d come to for a date night or a dinner with business partners, but there are also a number of kid-friendly eateries on these skyscraper-lined streets. Little ones will love grabbing a snack at Portillo's Hot Dogs, a true Chicago classic. Are sandwiches more their style? Al's Beef is a Windy City landmark for Italian beef sandwiches and burgers.
River North for Couples
What’s more romantic than a night at the theatre? River North is just a stone’s throw from Chicago’s Theater District. Put on your finest attire and walk across DuSable Bridge to watch a show at one of the Second City’s best theaters, just like Chicagoans have been doing for the past century. Catch Broadway musicals, drama, stand-up comedy, and more at the famous Chicago Theatre, the Goodman Theatre, and Cadillac Palace Theatre.
Though it actually sits northwest of Downtown Chicago, the East Village is one of Chi-Town’s most desirable areas for locals and tourists alike. You might also hear it called “Wicker Park” or “West Town,” so just know that it’s all the same place. This area is filled with restaurants, shops, and cafes that are often overlooked by the guidebooks, which means Chicagoans love this neighborhood even more. We’ll unveil some of the hidden gems just for you in this article, but we’ll keep some of them preserved to keep the peace with the locals.
Neighborhood Highlights: East Village
On the corner of style and luxury, Stay Alfred at The Ace on Ashland offers modern travel apartments in the heart of the East Village neighborhood. Kick back and relax on the rooftop deck, or enjoy some R&R on your own private balcony. Wondering where to stay in Chicago with the most modern amenities? Every unit here features classy quartz countertops and stainless steel appliances, plus a smart TV so you can pick up your favorite Netflix show right where you left off.
East Village for Friends
For a “village,” East Village has a vibrant nightlife and some fun places to hang out with friends. Enjoy a lazy afternoon at Emporium Wicker Park, a modern tavern with games and a vast selection of beers, or soak up the sun in famed Happy Village’s decades-old beer garden. They also have a ping pong table if you’re interested in practicing your serve. Another notable neighborhood bar is Innertown Pub, which features a pool table and a cash-only policy, so you can revel in the feeling of nostalgia for an age before Apple Pay. Or, for a cocktail experience that’s totally modern, check out The Violet Hour for some of the most creative drinks in town. Cheers!
East Village for Business Travelers
What’s one thing that will really set you up for success with a packed day of meetings ahead? A good cup of coffee, and, thankfully, you’ll find a plethora of coffee shops in the East Village area. If you like your java with a bit of time travel, check out The Wormhole Coffee. A visit is like getting sucked through the time-space continuum back to the 80s – there’s even a real DeLorean on display. More contemporary but just as good are Fairgrounds Coffee & Tea, Scone City, and Ipsento 606.
East Village for Families
If you happen to be in the East Village when the kids start screaming for ice cream, well, you’re in luck. This neighborhood has a higher density of ice cream shops than anywhere else in the city (by our not-so-scientific study), so you can dig into a frozen treat even during a blizzard. For some of the best gelato in town, check out Black Dog Gelato or Caffè Gelato, both serving ultra-creamy, flavorful goodness. They even give samples with those cute little gelato spoons.
For ice cream with a twist (or a roll, actually), Coco Rolled Ice Cream is your spot – especially if you like Nutella. For a healthy twist on frozen yogurt, check out The Lifeway Kefir Shop, which serves the nutritious fro-yo in kid-friendly flavors like strawbanana and chocolate. In the mood for an ice cream sandwich? Forget about those ice cream sandwiches in the freezer section with the cookie part that sticks to your fingers. Elevate your dessert game with a gooey, decadent sandwich made with warm chocolate chip cookies from Insomnia Cookies.
East Village for Couples
You’ll find the hottest name-brand stores near the Magnificent Mile, but here in the East Village, it’s all about shopping local. Pick up some unique souvenirs to remember your romantic escape to the Windy City at these eclectic East Village boutiques.
For European fashion for men and women, check out the locally owned Penelope's, where there’s always something new and interesting. Find vintage clothing and military-inspired gear at Belmont Army Wicker Park, where you never really know just what you’ll find. And anyone who’s nostalgic for the days of CDs and records will love browsing the shelves at Reckless Records. Have a furry friend back at home? Don’t forget to grab something for them at Doggy Style Pet Shop.
Back in the 1880s, Gold Coast became Chicago’s version of Beverly Hills as the city’s wealthiest residents moved north of the urban core. While Chicagoans weren’t splashing out on rooftop pools or state-of-the-art fitness centers back then, they certainly did have a taste for luxury and built some of the city’s most stately homes and apartment buildings. Home trends have changed, but Gold Coast’s exclusive reputation remains. In this neighborhood, you’ll find excellent dining and convenient access to the lakefront parks in addition to a myriad of historical landmarks.
Neighborhood Highlights: Gold Coast
It only makes sense that Gold Coast’s Stay Alfred at The Seneca would be packed with the finest amenities. From walk-in closets to quartz countertops, the travel apartments are just as luxurious as the building, which features high-end common areas like a game room, a coffee bar, indoor fireplaces, and a rooftop deck.
Gold Coast for Friends
You’re in the Windy City, so prepared to get blown away by some hilarious stand-up comedy. That’s exactly why you should visit the Gold Coast’s comedy clubs instead of listening to your travel apartment company’s lame jokes. Head over to The Second City, where many famous comics actually learned the art of stand-up. Seriously, this Chi-Town joke joint boasts alums like Tina Fey and Bill Murray, so, you never know, the star of that show you see with your pals next weekend might show up on SNL or Comedy Central one day!
Also worth a visit is Zanies Comedy Night Club, just a block away from The Second City, which welcomes touring and local talent with shows every single night. Even if you and your friends are in town on a Tuesday night and want to go out on the town, Zanies will be waiting for you with a cold beverage and an open seat.
Gold Coast for Business Travelers
Staying in Gold Coast but heading downtown for the work day? You’re not alone; in fact, scores of Chicagoans do the north-to-south commute every day – but only after they’ve enjoyed a hearty breakfast at a favorite cafe. Okay, not everybody goes out for breakfast every day, but if you’re only in town for a few days, why not treat yourself?!
Pull up a chair at 3rd Coast Cafe and order a farmers omelette, cinnamon raisin french toast, or a colorful veggie hash. This breakfast joint has been open for almost 100 years, but the food is fresh and delicious every day. If you like potatoes, then you can’t miss the spud-obsessed Hashbrowns Cafe, which specializes in – you guessed it – hashbrowns. But not just any ol’ hashbrowns; sweet potato hashbrowns, rosemary hashbrowns, and even the fully loaded hashbrowns, which are topped with sour cream, onion, cheese, and corn flakes (hello, crunch!). The eatery serves breakfast all day, so you’ll have time to try them all. Or, for a truly decadent breakfast that might send you straight into a food coma, try Do-Rite Donuts & Chicken, where you can dig into an egg sandwich on a donut or a creative take on chicken and waffles.
Gold Coast for Families
What kid doesn’t want to spend a day at the Chicago History Museum?! Okay, it might not sound super exciting, but these are not your average museum exhibits. Photos, films, and interactive events make Chicago’s storied past come to life in a way that will enthrall even the little ones. When the young’uns get hungry after some time in the museum, there’s no better way to spend the lunch hour than by indulging in some of Chi-Town’s finest deep-dish pizza. In the Gold Coast area, you’ll find standbys like Lou Malnati's and Giordano's (we won’t get into the debate about which one is better). Or, try a twist on the classic at Happy Camper, Mama Milano, or Sono Wood Fired.
Gold Coast for Couples
Sure, you can always order take-out or pick up a microwave-ready meal from the store, but sometimes a special occasion deserves a meal to remember. Chicago’s restaurant scene is one of the best in the country, so a date night featuring haute cuisine is the perfect way to spend a romantic evening. Planning in advance? These restaurants require reservations to be booked – sometimes months ahead of time.
Only a lucky few every night can enjoy the culinary destination that is Alinea. Earning three Michelin stars and the reputation of one of the best restaurants in the world, the tasting menu served here is a multisensory experience. It’s definitely a splurge, but you’ll remember it forever. Right across the street is Boka, with two Michelin stars, and the one-starred Spiaggia is also worth a visit toward the Magnificent Mile.
It may be the “South” Loop, but we think this neighborhood sits right in the middle of the action. Walk to the Museum Campus, waterfront parks, and tons of delicious places to eat, or hop on the L to access the northern part of Downtown in just minutes. We like the quiet, leafy atmosphere of the South Loop and its easy access to all the attractions.
Neighborhood Highlights: South Loop
Within walking distance of the Museum Campus and a slew of excellent restaurants, the upscale Stay Alfred at Park Michigan features a picturesque rooftop terrace with BBQ grills and a cozy resident lounge. The comfortable 2-bedroom travel apartments are perfect for families or groups of friends, unless you’d prefer to share a cramped hotel room. Get the space and privacy you deserve at this sophisticated Stay Alfred.
South Loop for Families
If you’re visiting Chicago with kids, you’d better put South Loop’s Museum Campus on the agenda. This impressive collection of museums and attractions will show the whole family that learning is fun – especially when learning has lake views! One famous resident of South Loop is the world’s largest T-Rex, whose skeleton is on display at the renowned Field Museum. This science museum is one of the world’s best. But the whole day doesn’t have to be about fossils; just a few minutes’ walk away is the Shedd Aquarium, a massive collection of (living) marine species, and the Adler Planetarium, which is totally out of this world.
Besides the museums, catching a Chicago Bears game at Soldier Field is always a bear-y good idea. And if the crowds and tickets and walking just sounds like too much excitement, nothing beats an afternoon with the kids on the shore of Lake Superior at 12th Street Beach.
South Loop for Business Travelers
During a long day of meetings, conferences, or training, sometimes the only thing a business traveler wants to do is take a walk in the park. In Chicago, the most obvious place for a stroll in the outdoors might be the enormous Grant Park, but the South Loop is home to smaller neighborhood parks that are just as green but a bit cozier. Take a wander through Dearborn Park, and, if you're so inclined, squeeze in a little workout on the fitness equipment situated throughout the park.
On a walk in Cotton Tail Park, you may spot a friendly rabbit or two, and at Coliseum Park, you will most certainly spot a few four-legged friends. Feeling contemplative? Take a seat on a bench in Chicago Women’s Park & Gardens and admire the flora and fauna. You may even catch a free community yoga class!
South Loop for Friends
Set out on a day of sightseeing with pals and hit all the most famous highlights. From the South Loop, head north and walk through Millennium Park to take the ultimate Chicago friend pic at Cloud Gate. Commonly referred to as “the Bean,” this massive metallic sculpture is possibly the most iconic Chicago landmark, and it makes an awesome backdrop for photos.
And there’s no better souvenir than photos from the top of the Willis Tower. The famous skyscraper’s 103rd-floor observation deck is within walking distance of the South Loop, though we recommend taking the elevator (not walking) to the top of the building.
Don’t forget to snap the obligatory lakefront shot! The 319-acre Grant Park runs adjacent to
Lake Superior, so you’ll find plenty of suitable photo spots there.
South Loop for Couples
Go back in time to an era before swiping right existed with South Loop’s historic, romantic attractions. Take a stroll around Buckingham Fountain in Grant Park, one of the world’s largest, grandest fountains. If you time your visit right, you can catch the 20-minute-long water show that starts at the top of every hour. Continue your walk to the The Art Institute of Chicago, because nothing is more romantic than admiring Monet’s beautiful landscapes together.
In the evening, you may want to watch the Chicago Symphony Orchestra at the Chicago Symphony Center, or you can head to Jazz Showcase to catch a live jazz show. Top off the lovey-dovey day with a dry martini at the dimly-lit M Lounge – shaken, not stirred.
See you in Chicago!
Now go, go like the wind! You can consider yourself an expert on Chicago’s best neighborhoods, so now it’s time to see them in person. Are you craving a gooey slice of deep-dish like we are? There’s no better time than now to book your Windy City getaway.
Whether you’re packing shorts, snow pants or stilettos (check our packing list to make sure you don’t forget anything), Chicago is sure to show you a good time. If we can assist in your travel apartment booking process in any way, just give us a ring at 1.866.232.3864 and we’ll be happy to help.