Magnificent Mile Vacation Packages
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Top Holiday Package Deals in Magnificent Mile
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
CA $1,046
per person
Dec 28 - Jan 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
El hotel es moderno y están perfectas las instalaciones. La amabilidad del Front Desk y el personal de paquetería es cuestionable, pero la ubicación lo vale.
Reviewed on Oct 22, 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
CA $965
per person
Dec 26 - Jan 2
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,173 reviews)
The kids loved the pool. Location for price was incredible. Definitely coming back
Reviewed on Oct 22, 2026
Where to stay in Magnificent Mile
Find the best Magnificent Mile areas and neighborhoods for the activities you enjoy most. Learn more about Magnificent Mile
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.
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.
West Loop
Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
Magnificent Mile Hotel Deals
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
Fully refundable
CA $257
CA $355 total
Nov 22 - Nov 23
includes taxes & fees
The Westin Michigan Avenue Chicago
909 North Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
CA $202
CA $291 total
Nov 22 - Nov 23
includes taxes & fees
8.8/10 Excellent! (1,219 reviews)
"Great bed and a very clean room and bath."
Reviewed on Oct 22, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $147
CA $175 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very good! (10,188 reviews)
"Historic hotel that has some upgrades and modern amenities. The lobby bar could use some upgrades and a second working elevator on the South tower would have been helpful on busy days."
Reviewed on Oct 22, 2026
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.
Frequently asked questions
How much does a Magnificent Mile vacation package cost?
Create unforgettable memories with our Magnificent Mile vacation packages, which start from only CA $746. Choose the hotels and flights that match your travel plans. Then, add on one or two tours or experiences for an incredible getaway.
How do I get a cheap travel package to Magnificent Mile?
Browse and book everything in one place with our Magnificent Mile vacation packages. We have deals on flights, hotels and more that'll keep your hip pocket happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotel options around the world to pick from, there are endless opportunities to mix and match all you want.
Where should I stay in Magnificent Mile?
Take the leg work out of sightseeing by staying in a hotel just around the corner from Magnificent Mile's biggest attractions. McCormick Place and Millennium Park are two of the most popular.
What are the top hotels in Magnificent Mile?
If it's your first time in Magnificent Mile, make a reservation at InterContinental Chicago Magnificent Mile, an IHG Hotel or The Westin Michigan Avenue Chicago. Both hotels offer friendly service and are favorites with many travelers.
How far in advance should I book my Magnificent Mile vacation?
Reserving your flights early with Expedia means one less thing to worry about. A number of air carriers advertise tickets up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, low prices to Magnificent Mile sometimes become available in the weeks leading up to departure.
What does an Expedia Magnificent Mile travel package include?
Expedia has all you need to book your Magnificent Mile escape, but what your package looks like depends on you. Pick from any combination of rental cars, flights and hotels. Looking for some tours or activities to fill in your time? Once you've made your booking, you can add them on too. No matter your budget or style, there's a package to meet your needs.
What should I know before booking a Magnificent Mile travel package?
Booking all the parts of your trip together is one of the best ways to save. Bundle your flights, car rentals and hotels into one little package. But it's not just hotels. Expedia features all types of properties, including vacation rentals such as beachfront villas and city residences. You've got loads of choices!
Can I choose my airline with a Magnificent Mile Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the flexibility to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Magnificent Mile vacation package?
Because we know life can throw you a few curveballs, the answer is yes. For more information, check out our Customer Service Portal. But generally speaking, if you've booked your Magnificent Mile vacation package in the last 24 hours, you may be able to cancel or change it without penalty. Your hotel, airline or car rental company may charge a fee if your booking is older than that.
Stay near popular Magnificent Mile attractions
Chicago Water Tower
9.0/10 (1,235 reviews)
You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
Lookingglass Theatre
10.0/10 (2 reviews)
You can enjoy a show at Lookingglass Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
Jean Baptiste Pointe Du Sable Homesite
Find out about the history of Chicago with a stop at Jean Baptiste Pointe Du Sable Homesite. Amble around this vibrant area's riverfront or experience its entertainment choices.
Things to do
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.