Chicago Vacations
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Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago
4 out of top 10 points of interest in this area
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Lake Michigan are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
Find the Best Chicago Vacation Packages
Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
SAR 418
SAR 497 total
8 Sep - 9 Sep
includes taxes & fees
8/10 Very Good! (10,288 reviews)
"Lower price$"
Reviewed on 11 August 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
SAR 537
SAR 638 total
31 Aug - 1 Sep
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
SAR 862
SAR 1,012 total
11 Sep - 12 Sep
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Chicago attractions
Photo by © City of Chicago
Wrigley Field
9.0/10 (11,704 reviews)
Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."
Navy Pier
9.0/10 (24,140 reviews)
This historic Chicago waterfront landmark offers panoramic lake views from its iconic Centennial Wheel. Enjoy seasonal fireworks or interactive exhibits at the Children's Museum while exploring Navy Pier.
Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Soldier Field blends historic neoclassical columns with modern design as home to the Chicago Bears. Experience the electric atmosphere of an NFL game or take a guided tour exploring its century of sporting heritage.
Photo by © Cesar Russ Photography
McCormick Place
8.8/10 (9,822 reviews)
McCormick Place hosts major events like the Chicago Auto Show in its 2.6 million square feet of exhibition space. Arrive via the convenient Metra Electric Line station directly beneath the complex.
Chicago Riverwalk
9.6/10 (13,574 reviews)
This 1.25-mile urban promenade showcases Chicago's stunning architecture alongside the river. Stroll past public art installations, dine at waterfront cafés, or catch the evening Art on theMART digital projection show.
Millennium Park
9.4/10 (30,446 reviews)
Discover Chicago's artistic heart at Millennium Park, home to the reflective Cloud Gate and interactive Crown Fountain. Stroll through Lurie Garden or catch a free concert at the Jay Pritzker Pavilion.
Six Flags Great America
8.6/10 (992 reviews)
This Midwest thrill-seeker's paradise boasts 15 roller coasters and immersive themed areas. Arrive at opening to conquer popular rides, or consider a Flash Pass to maximize your adventure.
Frequently asked questions
How much does a Chicago vacation package cost?
You'll find cheap prices on Expedia for your Chicago getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Chicago costs.
What are the cheapest months to go to Chicago?
December, January and February are the best times to look for cheap Chicago vacation packages. Opting to travel in quieter periods means you can typically find lower prices on accommodations and flights.
How to find the best Chicago package deals?
Use Expedia's filters to find some fabulous Chicago package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Chicago package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chicago vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking hotels and flights individually. Better still, you can tailor your Chicago trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Chicago?
If you're considering a spur-of-the-moment Chicago trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chicago?
- Choose the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit Chicago.
- Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Chicago.
- Decide how long to go away for: Now that you're more familiar with Chicago, you can work out the ideal length of your break. Pull together a rough plan and allocate enough time to get through everything on your must-do list.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalized Chicago vacation package.
