Magnificent Mile Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Holiday Package Deals in Magnificent Mile

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $2,730, price is now CA $1,207 per person
CA $1,207
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,734, price is now CA $2,634 per person
CA $2,634
per person
Dec 27 - Jan 2
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $3,785, price is now CA $2,704 per person
CA $2,704
per person
Dec 27 - Jan 2
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,000, price is now CA $1,481 per person
CA $1,481
per person
Dec 27 - Jan 2
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $4,492, price is now CA $3,391 per person
CA $3,391
per person
Dec 27 - Jan 2
found 15 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Always the best hotel in Chicago!!!!

Reviewed on Nov 2, 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.

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 $273 per night from Nov 22 to Nov 23
CA $273
CA $374 total
Nov 22 - Nov 23
includes taxes & fees
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 $185 per night from Nov 22 to Nov 23
CA $185
CA $270 total
Nov 22 - Nov 23
includes taxes & fees
8.8/10 Excellent! (1,219 reviews)
"Staff was great, but the hotel itself is a little tired. I was hoping for the heavenly bed and the room certainly didn’t have it (or maybe it was just old?). I would probably choose another hotel next time."

Reviewed on Nov 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 CA $162 per night from Nov 23 to Nov 24
CA $162
CA $193 total
Nov 23 - Nov 24
includes taxes & fees
Congress Plaza Hotel
See all 1,101 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 $1,207. 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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $57
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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.