Chicago isn’t just a city you visit. It’s a place you experience. The energy is contagious, and witnessing its combination of history and innovation will leave you feeling like you’re a part of something big. Live it up in Chicago and do it right by booking a Stay Alfred to make it a trip worth remembering.

Welcome to The Second City

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There’s simply nothing to do in Chicago. Unless, of course, you happen to be a fan of jaw-dropping architecture, world-class cultural events, gorgeous lake views, department stores like Bloomingdale’s and Barneys New York, and award-winning restaurants like The Signature Room at The 95th and Spiaggia. Sound like experiences you could learn to cope with? Then why not take your trip to the next level? Book a modern, spacious Stay Alfred the next time business or a vacation brings you to the Windy City. No matter what you’re into – art, culture, food, nightlife or any other of this great city’s winning charms, you’ll have the perfect luxury Chicago vacation rental to enjoy it from.

Chicago deep-dish pizza.
Chicago cubs lion statue with Chicago cub baseball hat.
Chicago ferris wheel under a dreamy sunset.
Chicago sea-horse fountain.
Famous Chicago theater sign.
Neighborhoods in

Chicago

Streeterville

Upscale and gleaming, Streeterville is the site of some of Chicago’s tallest buildings and to some of the most expensive real estate in the country. It’s also home to the attractions of Navy Pier, where you can enjoy carnival rides, shops, food and fireworks, to sandy Ohio Beach and, depending on what neighborhood-boundary authority you talk to, the Magnificent Mile- with its breathtaking night views. Dining, nightlife, retail and cultural experiences abound in this electric city and there are parks, museums and landmarks every other block. Streeterville is a happening little waterfront neighborhood and Stay Alfred has the place you can call home while you’re here.

River North

A neighborhood of warehouses until enterprising artists and shop owners began creating loft and retail spaces in the 1970s, River North is now home to art galleries, retail shops and high-energy nightlife in a neighborhood with a distinctly industrial feel. It’s also a just a short walk to the Magnificent Mile, and the Loop neighborhood is just across the river and easily accessible on foot. The variety and density of eateries and bars is nothing short of astounding. Every style of cuisine imaginable is available just steps away. You can take in the city views at the Chicago Riverwalk or catch a show at the House of Blues Chicago. No matter how you like to unwind, it’s likely you’ll find it in River North.

Chicago Loop

The loop – named for the elevated transit tracks that surround it – is Chicago’s central business district. It’s home to the iconic Cloud Gate (aka Bean) sculpture, green park spaces, the award-winning shows of the Theater District, and the Art Institute of Chicago – one of the country’s oldest and largest museums and home to famous works by Vincent van Gogh, Pablo Picasso, Georges Seurat, Edward Hopper and countless other artists. In town for a little retail therapy? Be sure to check out the shops on State Street – which also happens to be home to a wide variety of gourmet restaurants. Just what you need to keep your energy up while exploring all that this vibrant Windy City neighborhood has to offer.

Gold Coast

This neighborhood’s name didn’t happen by accident. In this part of town, you’ll find high-end boutiques (Barney’s, Armani, Chanel, Jimmy Choo, Tom Ford, etc.), fine dining (Gibsons Bar & Steakhouse, Nico Osteria, Le Colonial, Lou Malnati’s Pizza) – and an assortment of beyond-the-means-of-most auto dealers. When you book a travel apartment in this ritzy locale, you’re also just steps away from iconic works of architecture like the Old Chicago Water Tower and the Charnley-Persky House. If it’s arts and culture you’re looking for, the Gold Coast neighborhood is home to The Museum of Contemporary Art and the Broadway Playhouse. So many diversions for your consideration, dahhhling.

South Loop

The south end of Chicago’s massive Downtown district features some of the city’s best restaurants and things to do - with a more relaxed vibe than the fast-paced Magnificent Mile and riverfront areas. Here, you’ll find sprawling green spaces (highlights include Museum Campus and Northerly Island) and wide streets that are perfect for exploring on foot. There’s no shortage of cultural attractions, like the Field Museum, the Adler Planetarium, the Clarke House Museum (Chicago’s oldest surviving home), and entertainment venues like the Arie Crown Theater and the cozy M Lounge. And South Loop is ideal for all ages, with Soldier Field (home of the Chicago Bears) and the Shedd Aquarium calling this ‘hood home.

Find your place in the Windy City

Book your Chicago Stay Alfred today

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Alfred's local faves

It's just a short jaunt to these hip haunts

Food and Drink
Food and Drink
The Purple Pig

Named one of the “10 Best New Restaurants in America” -- try it and thank us later.

Food and Drink
Food and Drink
Flo & Santos

Pub meets pizzeria with Polish-American influences.

Food and Drink
Food and Drink
Beatrix

Healthy cafe and bakery by day, cocktail bar by night.

Arts and Entertainment
Arts and Entertainment
High Dive

An intriguing selection of American craft beers - and one of the best indie rock jukeboxes in Chicago.

Food and Drink
Food and Drink
Velvet Taco

Tantalizing “tacos without borders” that include globally inspired toppings and sauces.

Arts and Entertainment
Arts and Entertainment
John Hancock Center

Food and Drink
Food and Drink
Jake Melnick's Corner Tap

Chicken wings and a massive beer selection are the stars of this neighborhood pub.

Food and Drink
Food and Drink
Friends Sushi

Ultra-modern lounge serving sushi, sashimi, sake, and more.

Food and Drink
Food and Drink
Fig & Olive

Chic small plates with Mediterranean flair and a refreshing rooftop space.

Make a Stay Alfred Your Place in Chicago

Forget about staying in a boring, cookie-cutter hotel. Your Stay Alfred in Chicago is as warm and comforting as a deep dish pizza and as laid back and effortlessly cool as Ferris Bueller. Whether it’s a weekly apartment rental in Chicago you’re looking for or a place to stay for just a couple days, when you’ve got a great neighborhood at your doorstep and show up to a professionally cleaned, smoke free, high end apartment, you will be so happy that you’ll want to crash a parade and start singing on top of the main float. Seriously, let our helpful and friendly customer support staff sing right alongside you as you book your unforgettable Chicago vacation. They’re available round the clock, 24/7. So what are you waiting for? Book today!