Magnificent Mile Vacation Packages

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  • Better together

    Save up to CA $4,200 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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Top Holiday Package Deals in Magnificent Mile

Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,139, price is now CA $746 per person
CA $746
per person
Jul 9 - Jul 12
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Great location, nice property, extremely slow breakfast at in house restaurant Toro. Didn’t appreciate paying an “urban experience fee” with associated taxes.

Reviewed on Apr 24, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,409, price is now CA $895 per person
CA $895
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Breakfasr good, view great

Reviewed on May 1, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,836, price is now CA $1,194 per person
CA $1,194
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Clean the staff is very nice and polite

Reviewed on May 3, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,156, price is now CA $768 per person
CA $768
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (484 reviews)
small town main street neighborhood, good food nearby, shopping

Reviewed on May 1, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,509, price is now CA $1,012 per person
CA $1,012
per person
Jul 9 - Jul 12
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 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

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.

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 CA $270 per night from May 26 to May 27
CA $270
CA $369 total
May 26 - May 27
includes taxes & fees
9.2/10 Wonderful! (3,034 reviews)
Welcoming, accommodating, pampering and regenerating experience every time we stay at the Intercontinental. A wonderful place to enhance one’s Chicago experience.

Reviewed on Apr 29, 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
The price is CA $205 per night from May 25 to May 26
CA $205
CA $285 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (1,135 reviews)
Na

Reviewed on May 3, 2026

The Westin Michigan Avenue Chicago
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from May 25 to May 26
CA $118
CA $182 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,662 reviews)
Staff was wonderful.

Reviewed on May 3, 2026

Hotel Felix River North/Magnificent Mile
See all 1,135 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 $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.

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 fascinating museums.

Lookingglass Theatre

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
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.