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
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
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.
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.
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.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Find the Best Chicago Vacation Packages
Chicago Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
₩231,204
₩274,878 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (5,440 reviews)
"Great place to travel!"
Reviewed on Sep 25, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
₩219,443
₩260,896 total
Oct 26 - Oct 27
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
₩219,880
₩261,417 total
Oct 25 - Oct 26
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."
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.
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.
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 TM
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.
Photo by TM
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.
Michigan Avenue
9.4/10 (15,813 reviews)
Stroll down this iconic Chicago boulevard lined with luxury boutiques and historic architecture. Enjoy world-class shopping, acclaimed restaurants, or explore nearby cultural spots like the Art Institute.
Frequently asked questions
How much does a Chicago vacation package cost?
You'll find cheap prices on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel 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'll typically find lower prices on accommodations and flights.
How many days is enough for Chicago?
To fully enjoy a Chicago vacation, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue, Chicago Riverwalk and other well-known attractions, on top of experiencing neighborhoods like Central Chicago and Near North Side. If you've got some spare time, include a day trip or tour in your Chicago vacation itinerary.
Is it worth booking a vacation package to Chicago?
Chicago has everything you need for a fantastic trip — views, dining and culture are just the start. Whether you want to visit attractions like Navy Pier and Soldier Field, or take the road less traveled, you'll find plenty to do on your Chicago vacation.
How to find the best Chicago package deals?
Use Expedia's filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Chicago vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the freedom to create a customized Chicago vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Chicago?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.
How to plan a trip to Chicago?
- Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chicago.
- Set a budget: Factor in costs like flights, transportation and food when working out how much to put aside for your trip to Chicago. Then, choose a property that suits your budget, whether that's an affordable stay or a swankier getaway.
- Work out your trip length: Consider how long you'd like to spend discovering Chicago. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chicago vacation package that brings all your bookings together.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
