Magnificent Mile Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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

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    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Magnificent Mile

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.

Reviewed on Jan 6, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,469, price is now CA $930 per person
CA $930
per person
Mar 21 - Mar 27
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was CA $1,816, price is now CA $1,178 per person
CA $1,178
per person
Apr 27 - May 3
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
The view from my room was stunning

Reviewed on Feb 7, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,843, price is now CA $1,253 per person
CA $1,253
per person
Apr 27 - May 3
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
Great stay. Would come again.

Reviewed on Jan 19, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,424, price is now CA $972 per person
CA $972
per person
Mar 21 - Mar 27
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 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 showing a city

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
The price is CA $220 per night from Feb 22 to Feb 23
CA $220
CA $302 total
Feb 22 - Feb 23
includes taxes & fees
9/10 Wonderful! (2,793 reviews)
Yes

Reviewed on Feb 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 CA $174 per night from Feb 13 to Feb 14
CA $174
CA $245 total
Feb 13 - Feb 14
includes taxes & fees
8.8/10 Excellent! (1,102 reviews)
Dated

Reviewed on Jan 25, 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 CA $122 per night from Feb 9 to Feb 10
CA $122
CA $143 total
Feb 9 - Feb 10
includes taxes & fees
8/10 Very Good! (9,863 reviews)
Good location for many activities. Room was good but less than great.

Reviewed on Feb 7, 2026

Congress Plaza Hotel
See all 1,152 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $707. 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.

Discover the most popular places to visit in Magnificent Mile

Lookingglass Theatre

You can enjoy a show at Lookingglass Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Lookingglass Theatre

Things to do

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
96% of travellers recommend
Color Factory Chicago Ticket
See all activities in Chicago

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.