Choosing the Right Time to Visit Chicago
If you're flexible about the dates when you're going to be in Chicago, you have several factors to consider.
Is scoring a good deal on your hotel at the top of your priorities list? You'll want to visit the city during the winter, after the chaos of the Christmas season wears off. Rates are generally low in January, but they start to climb again as the weather warms up. November might also be a cheap time to go. Bear in mind that if you visit during the winter, you may have to deal with unfriendly weather conditions, so plan accordingly.
Spring and autumn are also good times to visit. These times are cheaper than summer, and they offer mild weather. However, you should have a list of indoor attractions to keep you busy in case rain starts to pour. It's always fun to take in the city's many museums.
Summer is the most popular time to visit Chicago. Understandably, hotel rates skyrocket during the sunny season. The advantage of going in summer is the warm weather, and you might also catch an event in the city. The Puerto Rican Parade and Festival, the Chicago Blues Festival, and the Chicago Pride Fest are all in June. In July, you might catch Taste of Chicago or the Square Roots Festival. August brings the Chicago Jazz Festival and the Chicago Air and Water Show.
Below is a chart of the current pricing seasonality of hotels and motels in Chicago, IL:
Averate Rates by Star Rating
Below are 3 charts displaying average nightly cost trends by star rating class in Chicago, IL. Analyze these illustrations to determine the cheapest months to book a room in Chicago for upcoming travels.
Chicago’s Luxury Hotels
4 Star Average Prices: $206.66
Want to feel like an A-list celebrity while you're in Chicago? When cost is a minor concern and you're looking for five-star treatment, check out the following Windy City hotels:
Trump International Hotel and Tower Chicago.
The Trump name is synonymous with over-the-top luxury, and this hotel is no exception. It is one of only 10 hotels in the world to have a Forbes five-star rating for both its hotel and its restaurant. Expect stunning views of the city and unrivaled service and amenities.
The Langham Chicago.
This landmark skyscraper, designed by Mies van der Rohe, invites guests to enjoy its gorgeous views and convenient location. It is close to the Loop, the Magnificent Mile, and Millennium Park. Inside the spacious rooms, you'll find handmade wood furnishings, large bathrooms, and other opulent touches.
The Waldorf Astoria Chicago.
This AAA five-diamond masterpiece of hospitality features an award-winning spa and health club, spacious rooms with large tubs that are perfect for soaking, and private bars. The rooms also have top-notch sound systems so you can plug in your iPod and immerse yourself in your signature sounds.
The Peninsula Chicago.
The Far Eastern vibe at The Peninsula will make you feel like you've been transported to a new realm of luxury. Stop by the spa to unwind before you head to the hotel's gourmet restaurant, and then retire to your room to soak in a beautiful view of the city.
Chicago’s Most Budget-Friendly Options
3 Star Average Prices: $123.69
If you're going to be too busy exploring the city to care much about how well-appointed your hotel is, you'll probably want to book a room that is as cheap as possible.
Hostelling International Chicago.
This one is a hostel rather than a hotel, but you're still getting affordable hospitality in one of the world's most captivating cities. The hostel is clean, the staff members are friendly, and you can expect to meet fellow travelers who can share their experiences and advice with you. There are between 8 and 10 beds per room.
Travelodge Hotel Downtown Chicago.
This hotel offers a convenient location downtown, making it easy for you to explore the sights and sounds of the city. Basic amenities, such as in-room coffeemakers and free HBO and Showtime, will make your stay as comfortable as it is affordable.
Chicago's Essex Inn.
When you stay here, you might score a room with a lovely view of Grant Park and Lake Michigan. In your room, you'll find colorful decorations, an LCD TV, and a comfy work desk. Complimentary shuttle services make it a breeze to get to Chicago's top attractions, including The Magnificent Mile. There is also on-site coin-op laundry.
The Congress Plaza Hotel in Chicago.
The Congress Plaza Hotel and Convention Center's building is more than 120 years old — it's the perfect place to absorb Chicago's history while you stick to your budget! The rooms are spacious, and many of them offer a view of Lake Michigan. Upgrade to a Deluxe room if you decide you have a little wiggle room in your wallet.