Visiting Chicago any time of year can be a treat, however if you’re sensitive to cold, winter visitors need to “bundle up”. The “Windy City” being the 3rd largest metropolitan city in the United States, is jam packed with things to see and do. Keep in mind, the city is directly on Lake Michigan and is the most “walkable” city in the U.S. they say, so bring those sneakers and leave the high heels for the evenings out on the town.
When to Visit Based on Price
The best time to visit Chicago for reduced rates and room availability is after Christmas during the winter months of January through March.
• Low Season: January through March is less busy. Average Daily Rates of:
- 2 Star: $38-$179
- 3 Star: $60-$319
- 4 Star: $135-$510
• High Season: June through September offers the best weather. Average Daily Rates of:
- 2 Star: $38-$179
- 3 Star: $60-$319
- 4 Star: $135-$510
Magic Savings Tip: Many of Chicago’s popular attractions and museums offer “free days”; so check visitor’s booths and hotel information centers for lists and coupons. Also, these attractions are busiest at mid day and early afternoons, so go early or late.
Refusing to be pigeon-holed into a single category, Chicago caters to every kind of traveler. The diversity of the city's attractions is matched by its accommodation. From the most luxurious to the more modest hotels, there are always deals to find in the "windy city".
Chicago is the largest and most visited city in the Midwest. With so much ground to cover you need to know where the most convenient places to stay are. It all depends on what Chicago highlights most interest you.
Sights you mustn’t miss
Between April and October a visit to the Buckingham Fountain rewards you with a spectacular light show. This fountain is one of the largest in the world with its four sea horses.
Another must see is the city of Chicago and beyond, from the to of the tallest building in the world, the Willis Tower.
Chicago has its infamous past of gangsters and crime, so what better do than take a “Chicago Gangster Tour”?
Visit the Biograph Theatre where FBI gunned down John Dillinger, and the Mount Carmel Cemetery and Al Capone’s final resting place.
Fun things to do
During summer months, enjoy one of the outdoor concerts at the Jay Pritzker Pavilion.
You should visit the two most popular museums in Chicago, the Museum of Science and Industry and the Field Museum.
Another popular destination is the largest U.S. collection of impressionist artwork located in The Art History Museum.
Evenings you may want to take in the Joffrey Ballet or Shakespeare Theatre.
On a sunny spring, summer or fall afternoon, strolling the Lincoln Park is a rewarding and pleasant experience. For the whole family the Brookfield Zoo supplies lots of fun and entertainment.
Wine and Dine Tips
When visiting Chicago there are two things you must do, eat a real Chicago Dog and dine in a real old time Chicago Diner. These diners are going away fast, and as part of history you should experience a diner lunch special at least once while you can. The food isn’t always 5 stars, but its good and won’t break the bank.
For your Chicago hot dogs, try Hot Doug’s, Superdawg, Gene and Judes, or Pluto’s.
If a fan of deep-dish pizza, you’re in the city that invented it, so ask around and find your pleasure.
If you want to visit one of the oldest “speakeasy” bar restaurants and “mob hangouts” of old, then head to “The Green Door Tavern” on New Orleans Street.
One of Chicago’s most favorite watering holes today, try one of their prohibition-style cocktails while scanning the great menu for lunch or dinner.
Day Trips
Visit Lake Geneva, Wisconsin for a day where you can visit shops, play some golf or maybe rent a boat and cruise.
You can also visit Starved Rock where you can have a “Grand Canyon” feeling while walking over 44 paths overlooking nature’s canyons.
Where to Stay
Chicago is the largest and most visited city in the Midwest. With so much ground to cover you need to know where the most convenient places to stay are.
Millennium Park is the most popular meeting point in town and its artistic structures are a huge attraction. The Allegro Chicago Hotel puts you in walking distance of this famous location and close to the upscale shopping found on the Magnificent Mile and State Street.
The Hotel Burnham or the Intercontinental Chicago are the perfect hotels for a vacation filled with museums, entertainment and fine dining.
Our recommendations in Chicago
The Allegro Royal Sonesta Hotel Chicago Loop
Located in Chicago's The Loop neighborhood, Kimpton Hotel Allegro is in the city center and near the beach. Water Tower Place and Navy Pier are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Chicago Riverwalk and Grant Park. Looking to enjoy an event or a game? See what's going on at United Center or Soldier Field. Our guests appreciate the hotel's central location.
Staypineapple, An Iconic Hotel, The Loop
Located near the beach, Staypineapple, An Iconic Hotel, The Loop is in Chicago's The Loop neighborhood, a walkable area with great shopping. The area's natural beauty can be seen at Grant Park and Millennium Park, while Navy Pier and John G. Shedd Aquarium are popular area attractions. Looking to enjoy an event or a game? See what's going on at Soldier Field or United Center. Our guests love the hotel's central location.
Hotel Felix River North/Magnificent Mile
Located near the beach, Hotel Felix Chicago is in Chicago's River North neighborhood, an area with good shopping. Chicago Theatre and Field Museum of Natural History are cultural highlights, and some of the area's popular attractions include Navy Pier and Lincoln Park Zoo. Check out an event or a game at United Center, and consider making time for John G. Shedd Aquarium, a top attraction not to be missed. Our guests appreciate the hotel's central location.
Inn of Chicago
In the city center, Inn of Chicago is in Chicago's Near North Side neighborhood, an area with great shopping. The area's natural beauty can be seen at Chicago Riverwalk and Grant Park, while Navy Pier and John G. Shedd Aquarium are popular area attractions. Lincoln Park Zoo and Skydeck Ledge are not to be missed. Our guests appreciate the hotel's central location.
The Royal Sonesta Chicago Downtown
Located on a river, Royal Sonesta Chicago Riverfront is in Chicago's The Loop neighborhood, an area with good shopping. Chicago Theatre and Field Museum of Natural History are cultural highlights, and some of the area's notable landmarks include Chicago Riverwalk and John Hancock Center. Navy Pier and John G. Shedd Aquarium are not to be missed. Our guests appreciate the hotel's central location.
Comfort Suites Michigan Avenue Loop
Located in Chicago's The Loop neighborhood, Comfort Suites Michigan Avenue Loop is in the business district and near a metro station. Michigan Avenue and Water Tower Place are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Chicago Riverwalk and Grant Park. Check out an event or a game at Soldier Field, and consider making time for Navy Pier, a top attraction not to be missed. Our guests appreciate the property's central location.
ACME Hotel Company
Located in Chicago's River North neighborhood, ACME Hotel Company is in the city center and near the beach. Chicago Theatre and Field Museum of Natural History are cultural highlights, and some of the area's popular attractions include Navy Pier and Lincoln Park Zoo. John G. Shedd Aquarium and Skydeck Ledge are not to be missed. Our guests love the hotel's convenience to public transportation: Grand Station (Red Line) is just steps away and Chicago Station (Red Line) is 6 minutes by foot.
Hotel Saint Clair- Magnificent Mile
Located near the beach, The St. Clair Hotel – Magnificent Mile is in Chicago's Near North Side neighborhood, an area with good shopping. Chicago Riverwalk and John Hancock Center are notable landmarks, and travelers looking to shop may want to visit Michigan Avenue and State Street. Check out an event or a game at Soldier Field, and consider making time for Navy Pier, a top attraction not to be missed. Our guests appreciate the hotel's central location.
Hotel Versey Days Inn by Wyndham Chicago
Located in Chicago's Lakeview neighborhood, Hotel Versey Days Inn by Wyndham Chicago is in the entertainment district and near the beach. The area's natural beauty can be seen at Lincoln Park and Chicago Riverwalk, while Briar Street Theatre and Lincoln Hall are cultural highlights. Check out an event or a game at Wrigley Field, and consider making time for Lincoln Park Zoo, a top attraction not to be missed.
The Godfrey Hotel Chicago
Located near the beach, The Godfrey Hotel Chicago is in Chicago's River North neighborhood, an area with good shopping. Chicago Theatre and Field Museum of Natural History are cultural highlights, and some of the area's popular attractions include Navy Pier and Lincoln Park Zoo. Looking to enjoy an event or a game? See what's going on at United Center or Soldier Field. Our guests appreciate the hotel's central location.
Royal Sonesta Chicago River North
Located near the beach, Kimpton Hotel Palomar Chicago is in Chicago's River North neighborhood, an area with great shopping. State Street and Michigan Avenue are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Navy Pier and Lincoln Park Zoo. Check out an event or a game at Soldier Field, and consider making time for John G. Shedd Aquarium, a top attraction not to be missed. Our guests love the hotel's central location.
Hilton Chicago
Located in Chicago's The Loop neighborhood, Hilton Chicago is in the city center and near the airport. Willis Tower and Chicago Riverwalk are notable landmarks, and travelers looking to shop may want to visit State Street and Water Tower Place. John G. Shedd Aquarium and Navy Pier are not to be missed. Our guests appreciate the hotel's central location.
Sheraton Grand Chicago Riverwalk
Located in Chicago's Near North Side neighborhood, Sheraton Grand Chicago is in the city center and on the riverwalk. Chicago Riverwalk and Navy Pier are notable landmarks, and the area's natural beauty can be seen at Grant Park and Millennium Park. Looking to enjoy an event or a game? See what's going on at Soldier Field or UIC Pavilion. Our guests appreciate the hotel's location for the sightseeing.
Crowne Plaza Chicago West Loop, an IHG Hotel
Near a metro station, Crowne Plaza Chicago West Loop is in Chicago's Near West Side neighborhood, an area with good shopping. The area's natural beauty can be seen at Chicago Riverwalk and Millennium Park, while Chicago Theatre and Field Museum of Natural History are cultural highlights. Looking to enjoy an event or a game? See what's going on at United Center or Soldier Field. Our guests appreciate the hotel's central location.
Hotel Lincoln, part of JdV by Hyatt
Located in Chicago's Lincoln Park neighborhood, Hotel Lincoln is in the entertainment district and near the beach. John Hancock Center and Chicago Riverwalk are notable landmarks, and some of the area's popular attractions include Lincoln Park Zoo and Navy Pier. Looking to enjoy an event or a game? See what's going on at Wrigley Field or United Center.
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Located in Chicago's River North neighborhood, Holiday Inn Chicago-Mart Plaza River North is in the city center and on a river. Chicago Riverwalk and Willis Tower are notable landmarks, and travelers looking to shop may want to visit Water Tower Place and Navy Pier. John G. Shedd Aquarium and Lincoln Park Zoo are not to be missed. Our guests appreciate the hotel's location for the sightseeing.