Chicago's a great town to visit on a weekend just for the fun of it. There's the Art Institute of Chicago and Museum of Science & Industry for those who appreciate cultural institutions. Culinary types should love indulging in the city's hottest neighborhood for dining and drinking. Architectural buffs should definitely book reservations for the official Chicago Downtown Architectural Walking Tour.
That's a great start, but why not step up your experience with a sweet package? The majority of local hotels offer them--and some will even customize a package for you--but we rifled through a couple hundred deals to spotlight some of the very best.
From a Jamaican-inspired staycation to a private helicopter tour for two, a number of properties offer the coolest collaborations in the Windy City.
Midwest Resident Rate at Hotel Allegro
The ultimate staycation for Midwesterners occurs at the newly renovated Hotel Allegro, located in the heart of the downtown theater district. It's also next door to Cadillac Palace Theatre, so guests who book tickets for shows don't have to travel far. Another sweet benefit is that there's an evening complimentary happy hour with appetizers and wine 5-6 p.m. every night in the lounge. The package also includes 20 percent off stays, half-off on valet parking and 1 p.m. late checkout. The deal is only available to residents of Illinois, Indiana, Ohio, Kentucky, Missouri, Iowa, Wisconsin, Michigan and Minnesota.
Book A Splash & Crash Weekend Party at Acme Hotel Co.
The chic Acme boutique hotel offers comfort, rock ‘n’ roll style and affordable prices. Its new Splash & Crash weekend package is for those who dig the idea of skiing, but would rather skip the cold--and slopes. It consists of an overnight stay in five standard rooms, plus the Bunny Slope lounge rental for two hours with $250 worth of drinks and a private bartender. There's also a Hair of the Dog package that comes with Advil, burgers, and Gatorade. There's also a hot tub in the Bunny Slope lounge, which is certain to take the party up a notch or two. It's for groups up to 18 people.
Romantic Package for Two at Dana Hotel
That late checkout is essential if you plan on spending it in bliss at the Dana Hotel with this incredibly romantic package. It starts at $509 and wraps up everything you'll need with an incredibly sexy bow. It includes a $300 gift certificate from luxury lingerie shop La Perla, sexy bath oils from the hotel's spa and a $20 dining credit to use at the restaurant. The hotel is also five minutes away from Lookingglass Theatre Company and in walking distance to some of the city's top blues clubs if you're considering taking in a show.
Private Helicopter Tour for Two at Fairmont Chicago
You'll feel like you're on top of the world if you book this high-flyin' package that includes a private helicopter tour for two. Fairmont Chicago, Millennium Park has created this deal that should certainly appeal to those celebrating a milestone anniversary. Along with transportation to and from the helipad, guests will receive complimentary champagne with souvenir flutes, a high-resolution digital photograph, and a rose. The helicopter experience is about $500 and lasts for 17 minutes.
Jamaican Staycation at Hard Rock Hotel
When it's way too hot to indulge in an authentic Jamaican vacation, this may be the next best thing. Hard Rock Hotel, located right off the Magnificent Mile, offers a Jamaican-inspired staycation year-round, beginning with a platinum room upgrade with breathtaking views of the city. The package also includes $20 credit for the Jamaican-focused Mr. Brown's Lounge (where guests may dine, drink and listen to live Jamaican music), 50 percent off the hotel's valet parking and samples of Mr. Brown's Lounge signature jerk sauce and recipe cards to take home.
Lil James Family Adventurer at James Chicago
For those bringing in the family for a weekend excursion, James Hotel features a special package certain to put a smile on the little ones' faces. It includes four tickets to the Chicago Children's Museum, milk-and-cookie turndown service, a welcome amenity from hotel partner Seedling, a full list of DVDs to watch in-room, kid-friendly dining menus from David Burke’s Primehouse, and a selection of books and classic board games.
Club and Suite Retreat at Langham Chicago
The glorious British import is ideal for a romantic rendezvous, especially because your package allows you a spectacular view of the Chicago River. The best way to experience the Langham is to book a minimum of two nights in one of the club level rooms or suites. That'll allow access to the club lounge, where guests get a complimentary daily breakfast for two, evening cocktails, VIP amenity, personalized butler service and hotel credit of $100 per day. That may be used toward spa treatments and parking. The Langham is located in the heart of River North, and many restaurants and drinking establishments are within walking distance.
Stay for Breakfast at the Renaissance Blackstone Chicago Hotel
The historic luxury hotel has played host to 12 U.S. presidents, as well as celebrities and high-profile gangsters such as Al "Scarface" Capone since it opened in 1910. With this special breakfast package, families can feel like VIPs, too. It includes a contemporary American breakfast for two adults and children 12 and under at Mercat a la Planxa. That consists of dishes like brioche French toast topped with smoked honey butter, shrimp and grits, and the Blackstone Benedict with toasted brioche, chorizo, truffled hollandaise and breakfast potato.
Shedd Aquarium Package at Swissotel Chicago
In close proximity to Navy Pier is the Euro-centric Swissotel Chicago, which offers a cool package for those looking to take in the sights of the city. Hotel guests get two VIP Shedd Aquarium tickets with access to the Abbott Oceanarium, Aquatic Show, the sharks in Wild Reef and more. There's also breakfast for two in the hotel's restaurant and complimentary use of the 42nd-floor fitness center and pool.
Very Important Pups Package at Thompson Chicago
Traveling with your pet? Thompson Chicago's newest program features a premium service that pampers your pooch. It comes with branded food and water bowl, dog toys and bandana upon check-in. There are also customized dog bones, dog bed, shopping passes for 15 percent off at the Tails in the City pet boutique and a "Pets in the City" guide to Chicago. The Gold Coast hotel is also home to the award-winning, seafood-focused Nico Osteria and is across the street from Gibsons Steakhouse.
Family Fun Package at theWit
Because of the infamous Roof cocktail lounge, most folks think of theWit as a party hotel. It's also very family friendly as it offers a family fun package and is close to many attractions (Art Institute, Goodman Theatre, Chicago Symphony Center). Included in the package is breakfast for four, premium wifi and late checkout.