If you’re looking for information on where to stay in Chicago IL then we have some great recommendations for you! Penthouses are a way to travel luxuriously yet affordably, especially when traveling in a group. Where to stay in Chicago IL does not have to be a challenging and time-consuming question. Here we’ve put together a straightforward list to help you find your perfect Chicago accommodation, penthouse-style! Also included are the best nearby local attractions. Your quest regarding where to stay in Chicago IL starts now!
Chicago, with its over 2.7 million inhabitants, is the most populous city in both Illinois and the Midwest United States. Bordering Chicagoland is Lake Michigan to the east and several suburbs to the north, west and south. Altogether the Chicagoland area is home to roughly 10 million people.
Chicago is largely known for its sports, food and finance. Chi-town is one of the few United States cities with two professional baseball teams, the Chicago Cubs on the Northside and the Chicago White Sox on the Southside. The Chicago Bears (football), the Chicago Blackhawks (hockey) and the Chicago Bulls (basketball) make up the other professional teams. Great food can be found throughout Chicagoland. The finance and big business sector is located in the south Loop area, where the Chicago Board of Tradeand Willis Tower are located.
This most populous Midwest city is home also to some very fine museums such as the Museum of Science and Industry, The Field Museum, The Art Institute, Adler Planetarium, Shedd Aquarium and The Museum of Contemporary Art. Lincoln Park Zoo is a fun and free experience, especially for the kids.
Where to stay in Chicago IL is a great question and we think you’ll find your perfect accommodation from the list below.
Reserve Collection Penthouse offers 3 bedrooms, a living room, a fully equipped kitchen, free WiFi and air conditioning. Near this Loop penthouse you’ll find: The Dearborn (urban American tavern), Magnolia Bakery, Disney Store, Latinicity (food hall + lounge), AMC DINE-IN Block 37 (movie theater), Block 37 (shopping mall), Godiva Chicago, CHANEL, Macy’s, Old Navy, Argo Tea, Garrett Popcorn Shops, Paul Young Fine Jewelers, James M. Nederlander Theatre, Gene Siskel Film Center, Roti Modern Mediterranean, Atwood (seasonal American fare), Nordstrom Rack, H&M and more.
Approximate cost per night: $1,240
Cost per person (ten people): $124
Thompson Chicago offers a penthouse suite and amenities such as an on-site restaurant, a fitness center, free daily newspapers, coffee and tea, free WiFi, flat-screen TVs, minibars, bathrobes, deluxe bath amenities and modern rain shower-heads. It’s near: Nico Osteria (Italian restaurant), Shinola (watch store), The Frye Company (shoe store), Starbucks, Stil Salon & Spa, Brilliant Earth (jeweler), COS (clothing store), Del Frisco’s (steakhouse), Fabbri Furs, Christian Louboutin, TOM FORD, Fig & Olive (Mediterranean restaurant), Charles Ifergan (hair salon), Jimmy Choo, Tavern on Rush, Luxbar, The Original Pancake House, Carmine’s, Gibsons Steakhouse, Hugo’s Frog Bar and more.
This property is 0.3 miles from Oak Street Beach, 0.4 miles from Water Tower Place, Chicago Museum of Contemporary Art and Michigan Avenue, 1.4 miles from Navy Pier and 15.2 miles from O’Hare International Airport.
Approximate cost per night (penthouse suite): $1,423
With a penthouse suite option, free WiFi, seating areas, desks, air conditioning, linens, towels, flat-screen TVs, mini-bars a 24-hour front desk, a onsite bar/restaurant and cafe, Freehand Chicago is near: Pizzeria Uno, Fleming’s (steakhouse), The Dinner Detective (dinner theater), Weber Grill, The Berkshire Room (lounge), Pops for Champagne (wine bar), Watershed (bar), L.A. Burdick Chocolates, Alliance Patisserie (pastry shop), Adagio Teas, sweetgreen (salad shop), Nespresso USA, Bloomingdale’s, Eataly (Italian restaurant), Joe’s (seafood), Sable Kitchen & Bar and more.
This location is 0.2 miles from Chicago Tribune Tower and Wrigley Building, 0.3 miles from Michigan Avenue and House of Blues, 0.7 miles from Millenium Park, 1 mile from Willis Tower and 15.4 miles from O’Hare International Airport.
Approximate cost per night: $1,549
Cost per person (six people): $258
FieldHouse Jones resembles a field-house and has an on-site bar and restaurant, a 24-hour front desk, a gymnasium lounge, a coffee bar, seating areas, flat-screen TVs, free toiletries and hair dryers. This hotel is near: BIG & little’s Restaurant, Steven Deer Salon, Millennial Mart, Marwen, Kiki’s Bistro (French Restaurant), Savage Smyth (event venue), Revitalab (spa and health club), Mogadishu Restaurant, Bismilahi Restaurant, Flex Pilates Chicago, Haute Living (furniture store), Headquarters Beercade (bar & grill), Good Measure (bar), Farmhouse Chicago (American restaurant), Steves Place (American restaurant), Paper Source (stationery store), Griddle 24 (diner), KC Chocolatier (chocolate artisan) and more.
Oak Street Beach is 700 feet, Michigan Avenue is 0.7 miles, Navy Pier is 1.7 miles, Wrigley Field is 3.6 miles and O’Hare International Airport is 14.8 miles from this location.
Approximate cost per night: $341
Cost per person (six people): $56
The Penthouse at Grand Plaza offers a rooftop swimming pool, a sun deck, a fitness center, a basketball court, 3 bedrooms, 3 bathrooms, 3 balconies, free WiFi, floor-to-ceiling windows, a fireplace, a fully-equipped kitchen, a dining area and laundry facilities. It’s close to: Bed Bath & Beyond, Cold Stone Creamery, Gelato D’Oro (Italian restaurant), Eggsperience Cafe, M Burger, Osteria Via Stato (Italian restaurant), Weber Grill, The Dinner Detective, Fleming’s Prime Steakhouse, Pizzeria UNO, Broken Shaker (cocktail bar), The Berkshire Room (lounge), Rock Bottom Restaurant, Cantina Laredo (Mexican restaurant), Corey’s NYC Bagel Deli, Grossman & Jack Talent and more.
Marina City, House of Blues and Michigan Avenue are 0.3, Art Institute of Chicago is 0.9 miles, Willis Tower is 1 mile and O’Hare International Airport is 15.4 miles from this location.
Approximate cost per night (three-bedroom penthouse): $1,587
Cost per person (eight people): $198
In the vicinity?
Offering 3 bedrooms, a living room, a fully-equipped kitchen with dishwasher and microwave, a flat-screen TV, a washing machine, city views and free WiFi, this loop penthouse is close to: Ajida Ramen, Jo Chicago (hair salon), Surmesur (custom menswear), Prime & Provisions (fine dining restaurant), Costa Vida (Mexican restaurant), Boar’s Head Cafe, Veggie Grill, Goodwin’s (American restaurant), Mixed Greens (salad shop), Diana’s Nail & Spa, Whimsical Candy, 5411 Empanadas, Big Shoulders Coffee, Rosati’s (pizza restaurant), Asada Chicago (Mexican restaurant), La Cocina (Mexican restaurant), Crepe Bistro (French restaurant), Off the Tracks Grill, The UPS Store, Monk’s Pub, Pierogi Heaven, Philip Di Ciminna Barber Shop and more.
Chicago River Walk and Cadillac Palace Theatre are 0.1 miles, Lyric Opera of Chicago is 0.3 miles, Willis Tower is 0.5 miles, Navy Pier is 1.6 miles and Midway International Airport is 8.8 miles from this location.
Approximate cost per night (three-bedroom penthouse): $670
Cost per person (eight people): $83
(high demand – book in advance)
This Wicker Park hotel has a penthouse suite, free WiFi, hardwood floors, 400 thread sheets, flat-screen TVs, an on-site cafe and is near: Cafe Robey, Le Labo Fragrances, Fairgrounds Cafe, Pork & Mindy’s (sandwich shop), reishi (health and beauty shop), The Tankard (pub), TOMS Chicago (shoe store), ENSO Sushi & Bar, Dimo’s Pizza, Shinola (watch store), Timbuk2 (bag store), Potbelly Sandwich Shop, lululemon, The North Face, Northside Bar, benefit (beauty salon), Real Good Stuff Co. (juice shop), Starbucks, Bonci Pizza, Subterranean (bar), Estelle’s (bar), Chop Shop (American restaurant), Tapster (bar), Angry Pig Tavern and more.
The Robey is 1 mile from Congress Theater, 2.1 miles from United Center, 2.2 miles from Second City and Lincoln Park Zoo, 2.8 miles from Wrigley Field and 12.5 miles from O’Hare International Airport.
Approximate cost per night (penthouse suite): $699
(high demand – book in advance)
Measuring 2,500 square feet this two-bedroom Wicker Park Penthouse can be found near: I Love Kickboxing, Modern Gentlemen Salon, Celebrity Skin, Infiniteus (juice bar), The Delta (cocktail bar), Orange Theory Fitness, Salon Blonde, North Bar, Avenue N Guitars, Gallery Cafe, Uni Sushi, Diplomatic Seventeen Fifty (consignment shop), Pure Barre (fitness class), Las Palmas (Mexican restaurant), Lucia (Italian restaurant) and more.
From here you’ll find Steppenwolf Theatre 1.2 miles, DePaul University – Lincoln Park Campus and Congress Theater 1.3 miles, The Noble Horse Theatre 1.7 miles, Second City, Oak Street and Lincoln Park Zoo 1.9 miles, Wrigley Field 2.8 miles, Millennium Park 3.1 miles and Chicago O’Hare International Airport 12.9 miles.
Approximate cost per night: $515
Cost per person (four people): $128
What’s going on?
Steps from Michigan Avenue, this corner balcony penthouse is close to: Holy Name Cathedral Parish, Chick-fil-A, Loyola University of Chicago, Alfredo’s Barber Shop, Friends Ramen, Friends Sushi on State, Golden Needle Tailoring, Devon Seafood Grill, Sunny Side Up & Coffee Shop, Sport Clips Haircuts, Giordano’s (pizza), Potbelly Sandwich Shop, Downtown Dogs, Pippin’s Tavern, Streeter’s Tavern, Stiles Chiropractic Offices, Flaco’s Tacos, Wow Bao (Chinese restaurant), Forever Yogurt and more.
Water Tower Place is 0.2 miles, Millennium Park is 1 mile, Willis Tower is 1.3 miles and O’Hare International Airport is 15.3 miles from this location.
Approximate cost per night: $743
Cost per person (five people): $148
Printers Penthouse has 3 bedrooms, a fully-equipped kitchen with dishwasher and microwave, a flat-screen TV, free WiFi, a shared lounge, 24-hour front desk, spa and wellness facilities with a hot tub and sauna and an on-site casino. You will find close to this location: Umai, LO Spa and Nails, Pat’s Pizza, Sociale (small plates restaurant), Dollop Coffee, Half Sour (cocktail bar), First Draft (craft beer house), South Loop Strength & Conditioning, Sofi Restaurant (Italian restaurant), Sandmeyer’s Bookstore and more.
This location is 0.4 miles from the Chicago Board of Trade, 0.5 miles from Willis Tower, 0.6 miles from Art Institute of Chicago and Union Station, 0.9 miles from Shedd Aquarium and 15.8 miles from O’Hare International Airport.
Approximate cost per night: $893
Cost per person (six people): $148
So there you have it, a concise list of Chicago’s top penthouse rental options. We hope that you have found this information as wonderful as we have and most of all, that you enjoy your Chicago trip!