Save Big With Chicago Hotel Deals from Groupon
Deep dish pizza, architecture river tours, a stunning lakefront, and one of America's great live music scenes. Chicago delivers in ways that surprise most first time visitors. The Loop keeps you central and walkable, while River North and Wicker Park offer distinct neighborhood energy. Chicago hotel deals are competitive year round, with the strongest rates appearing in winter when demand drops and the city opens up.
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Chicago Guide
For a quick intro to what makes Chicago great, it’s hard to beat a ride down Lake Shore Drive, the 19-mile stretch of road running along the city’s eastern edge. On one side, you’ve got sparkling Lake Michigan, and, on the other, a string of show-stopping skyscrapers and the city’s "front yard," Grant Park, home to the Lollapalooza festival and Buckingham Fountain.
What to Know Before You Go
- Best time to visit: between Memorial Day and Labor Day. The weather can be sticky and the lakefront overcrowded, but summer is Chicago’s time to shine. Knowing the warm temperatures won’t last long, locals take every opportunity to be out and about. There are street parties and music festivals nearly every weekend.
- City of neighborhoods: Chicago encompasses a large and diverse collection of neighborhoods, each with its own personality. Try a gyro in Greektown, walk through the National Museum of Mexican Art in Pilsen, or catch a Cubs game at Wrigley Field in Lakeview.
- Forget the car: Traffic in the city can be unrelenting, and parking is expensive. Consider relying instead on the L, Chicago’s elevated train, or taxis—especially if you’re only in town a short while.
Chicago for Foodies
It’s not all about hot dogs and deep-dish pizza anymore. In recent years, the Windy City has garnered lots of attention for its cutting-edge culinary scene. Food & Wine magazine named it one of the 10 Best Restaurant Cities in the world in 2008. The West Loop neighborhood, in particular, has become a popular landing spot for celebrity chefs.
- The Aviary: Bartenders inject bourbon, sugar, and bitters inside hollow balls of ice at this ambitious cocktail joint. It was recently named the country’s most Outstanding Bar Program by the James Beard Foundation.
- Girl & the Goat: Top Chef winner Stephanie Izard creates inventive dishes from unconventional cuts of meat, including oven-roasted pig face and duck tongue. Plan ahead, though—reservations fill up months in advance.
- Au Cheval serves up the best burger in the country, according to Bon Appetit. It’s right across the street from Girl & the Goat.
- Where to stay: The Crowne Plaza Chicago Metro hotel is conveniently located near all of the above restaurants, as well as Greektown.
Chicago for Arts Lovers
- Museum Campus: a 57-acre complex along the lake that’s home to three of the city’s best educational institutions. You can watch shark feedings in a 90,000-gallon tank at Shedd Aquarium, go star-gazing at Adler Planetarium, or head to the Field Museum to see the largest and most complete Tyrannosaurus rex fossil ever unearthed
- Steppenwolf Theatre Company in Lincoln Park is the gold standard for Chicago-style theater—gritty, gutsy plays produced by a fearless ensemble. Several of the troupe’s productions have transferred to Broadway, including a Tony-winning staging of Who’s Afraid of Virginia Woolf?
- The Second City: This 50-year-old sketch-comedy theater in Old Town launched the careers of Tina Fey, Amy Poehler, Stephen Colbert, John Belushi, and a host of other funny people.
- The Art Institute of Chicago has an embarrassment of riches, including Grant Wood's American Gothic, Edward Hopper’s Nighthawks and a slew of Impressionist masterpieces.
- Where to stay: Swissotel, a sleek hotel in the Loop, is just a short walk from the Art Institute and the beloved architectural boat tours along the Chicago River.
Chicago for Shoppers
- The Magnificent Mile: This famous retail corridor along North Michigan Avenue is a window-shopper’s paradise, with outposts from fashion icons such as Burberry, Chanel, Tiffany, and Neiman Marcus.
- River North features dozens of art galleries, many of them housed in converted warehouses. This is the best place to check out work by emerging artists.
- Randolph Street Market: Shop for antiques and vintage furnishings at this European-style indoor-outdoor market.
- Where to stay: Between purchases, you can partake in afternoon tea at the Drake Hotel—a tradition that was once enjoyed by Princess Diana and Queen Elizabeth II—or follow in the footsteps of Brad and Angelina, who prefer the extravagance of The Peninsula hotel on East Superior Street.
Frequently Asked Questions
For centrally located Chicago stays near Millennium Park, the Riverwalk, or the Magnificent Mile, a solid deal typically runs around $110 to $140 per night for 3–4 star hotels, with occasional promos dipping closer to $100 in slower periods. Suburban options like Buffalo Grove or Oak Brook can drop into the $80 to $120 range while still offering pools and free Wi‑Fi.
The most budget-friendly times to book Chicago hotels are usually late fall and early spring, when nightly rates can be 20–30% lower than peak summer. Avoid major event weekends like Lollapalooza or the Chicago Marathon, when downtown prices and availability tighten dramatically.
Several Chicago-area properties let kids stay free, which can shave a significant amount off a family trip. Options like the Warwick Allerton on the Magnificent Mile, The Godfrey in River North, and the Congress Plaza on South Michigan Avenue all highlight children staying at no extra room charge on select offers.
To stay by Millennium Park and the lakefront with a discount, look at downtown properties such as Arlo Chicago, Radisson Blu Aqua, or Le Méridien Essex, which frequently run member-only pricing. Locals often track these special rates through limited-time promotions and member dashboards instead of paying flexible rack rates.
Travelers wanting to be right at Navy Pier can book Sable at Navy Pier Chicago, where rooms overlook Lake Michigan and entertainment is steps away. While rates often start around the mid-$200s, you’re effectively combining lodging with front-row access to the pier’s dining, rides, and boat tours.
Chicago visitors planning group or friends’ trips often choose River North properties that highlight shared spaces and larger rooms. The Chicago Hotel Collection River North, AC Hotel by Marriott, and all-suite spots near the Magnificent Mile frequently promote group-friendly layouts and occasional member pricing that lowers the per-person cost.
Staying near O’Hare at places like Residence Inn Chicago O’Hare or nearby suburban hotels in Rosemont gives you suite-style rooms and lower nightly rates, often around $115 to $135. With the Blue Line train and expressways, you can usually reach downtown Chicago in about 35–45 minutes while saving on parking and city-center prices.
Yes, resort-style stays such as Hyatt Lodge in Oak Brook or Eaglewood Resort and Spa in Itasca offer pools, spa or golf amenities, and wooded grounds while keeping you within a reasonable drive of downtown. These suburban retreats typically start around the mid-$130s to low-$170s per night, especially outside peak weekends.