Magnificent Mile Vacations from ¥338,580

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The Latest Magnificent Mile Vacation Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

Downtown Chicago
¥338,580
per person
Nov 15 - Nov 20
found 19 hours ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9/10 Wonderful! (1,119 reviews)
We felt welcome and safe. Everything went smoothly and easy to stay.

Reviewed on Sep 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥394,474
per person
Nov 15 - Nov 20
found 19 hours ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥354,634
per person
Nov 15 - Nov 20
found 19 hours ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Hotel was clean and well kept. The staff were friendly and helpful. Great location as well

Reviewed on Sep 4, 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥434,350
per person
Nov 15 - Nov 20
found 19 hours ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.8/10 Exceptional! (1,018 reviews)
It was not worth what I paid. The spa was a disappointment. The steam rooms and sauna were small and uncomfortable. One of the steam rooms had missing tiles and loose tiles. I did not care for the pool. Check-in went well and the rooms were good size. The beds were comfortable. However, the rooms are not sound proof. I was on the top floor and I could hear the noise from the street. I will stay somewhere else on my next visit.

Reviewed on Sep 5, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
¥343,314
per person
Nov 15 - Nov 20
found 19 hours ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
8.8/10 Excellent! (2,341 reviews)
The staff were amazing and helpful!

Reviewed on Sep 5, 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
A busy city street with tall buildings, a bus, and cars.

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.

A river with yellow boats, a bridge, and tall buildings.

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.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

A wooden pavilion with a view of a city skyline and a body of water.

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.

A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

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).

Magnificent Mile Hotel Deals

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave Chicago IL
¥32,111
¥43,646 total
Sep 8 - Sep 9
includes taxes & fees
InterContinental Chicago Magnificent Mile by IHG
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

909 North Michigan Ave Chicago IL
¥27,971
¥38,829 total
Sep 7 - Sep 8
includes taxes & fees
The Westin Michigan Avenue Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
¥16,138
¥19,187 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (10,281 reviews)
"Rude staff. Not clean. Everything is run down. Not worth the money."

Reviewed on Sep 5, 2026

Congress Plaza Hotel
See all 1,107 properties in Magnificent Mile
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 ¥338,580. 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.
See properties

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.
See properties

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.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,272
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,453
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

¥6,484
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.