Magnificent Mile Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Breakfast and dinner served
    Aug 12 - Aug 19

    Omni Chicago Hotel + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.2/10 - Wonderful (1,789 reviews)
    "Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too."
    Reviewed June 3, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - HND • 1 stop
    ￥482,812
    ￥401,343
    per traveler
    found 1 day ago
    Omni Chicago Hotel
  • Front of property
    Aug 12 - Aug 19

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.4/10 - Exceptional (4,341 reviews)
    "Great location and roof top bar!! The hotel is new and the decoration is beautiful!! Room was good and clean. The only thing I didn’t like was the bed … it was too soft. I hope they sdd boiled eggs as an option for breakfast"
    Reviewed June 5, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - HND • 1 stop
    ￥551,979
    ￥425,798
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Terrace/patio
    Aug 12 - Aug 19

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    7 nights
    5.0 star property
    9.6/10 - Exceptional (1,881 reviews)
    "⭐⭐⭐⭐⭐ Amazing stay! Beautiful hotel, incredible views, excellent service, and a perfect location in downtown Chicago. Everything exceeded our expectations. We loved every minute of our stay and would definitely return. Highly recommended!"
    Reviewed June 4, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - HND • 1 stop
    ￥732,594
    ￥578,309
    per traveler
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Indoor wedding
    Aug 12 - Aug 19

    Swissotel - Chicago + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.0/10 - Wonderful (3,363 reviews)
    "Location is closer to Navy pier. Not a lot of nice food options around."
    Reviewed June 3, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - HND • 1 stop
    ￥528,920
    ￥423,297
    per traveler
    found 1 day ago
    Swissotel - Chicago
  • 2 restaurants; breakfast, lunch, and dinner served
    Aug 12 - Aug 19

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.4/10 - Exceptional (3,724 reviews)
    "Great location, excellent room and amenities proactively attentive staff."
    Reviewed June 4, 2026
    Roundtrip • Tokyo (HND) - Chicago (ORD)
    HND - ORD • 1 stop ORD - HND • 1 stop
    ￥539,063
    ￥448,734
    per traveler
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton

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

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Magnificent Mile Hotel Deals

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave Chicago IL
Fully refundable
The price is ￥31,202 per night from Jul 1 to Jul 2
￥31,202
￥42,698 total
Jul 1 - Jul 2
includes taxes & fees
9.2/10 Wonderful! (3,079 reviews)
"Clean room, helpful staff, and accessible. Close to everywhere food and shopping"

Reviewed on Jun 4, 2026

InterContinental Chicago Magnificent Mile by IHG
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥30,242 per night from Jul 2 to Jul 3
￥30,242
￥40,754 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (1,146 reviews)
"Rooms were small and outdated, nice location but overpriced for amenities."

Reviewed on Jun 4, 2026

The Westin Michigan Avenue Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥22,307 per night from Jun 29 to Jun 30
￥22,307
￥26,520 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,171 reviews)
"Good spot. Nice staff. Great location."

Reviewed on Jun 5, 2026

Congress Plaza Hotel
See all 1,117 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 . 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,236
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,904
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,276
per adult
92% of travellers recommend
Art Institute of Chicago
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.