Magnificent Mile Holidays from NZ$11,381

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was NZ$11,894, price is now NZ$11,381 per person
NZ$11,381
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Terrible mattresses, old and crunchy or something; bad lumpy pillows. No coffee or water in the room. If you want free coffee, you gotta track to the lobby during coffee hours and pay a "resort" fee for the experience.

Reviewed on 17 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was NZ$12,877, price is now NZ$11,904 per person
NZ$11,904
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug. 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was NZ$12,953, price is now NZ$12,102 per person
NZ$12,102
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug. 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was NZ$11,965, price is now NZ$11,424 per person
NZ$11,424
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug. 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was NZ$13,982, price is now NZ$13,372 per person
NZ$13,372
per person
30 Oct - 2 Nov
found 1 day ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
The most beautiful hotel !

Reviewed on 17 Aug. 2025

Our guide on 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 featuring 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

Our pick of the best 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 NZ$488 per night from 1 Sept to 2 Sept
NZ$488
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (2,212 reviews)
"Second time staying here and never fails to impress"

Reviewed on 16 Aug. 2025

InterContinental Chicago Magnificent Mile by IHG
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$269 per night from 2 Sept to 3 Sept
NZ$269
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (2,918 reviews)
"Excellent location"

Reviewed on 19 Aug. 2025

Warwick Allerton - Chicago
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
540 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$470 per night from 1 Sept to 2 Sept
NZ$470
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Great hotel"

Reviewed on 17 Aug. 2025

Chicago Marriott Downtown Magnificent Mile
See all 1,200 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 holiday package cost?
Create unforgettable memories with our Magnificent Mile holiday packages, which start from only NZ$11,381. 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 holiday 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 favourites with many travellers.
How far in advance should I book my Magnificent Mile holiday?
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 holiday homes such as beachfront villas and city residences. You've got loads of choices!
Can I choose my airline with a Magnificent Mile Expedia holiday 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 holiday 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 holiday 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

Chicago Water Tower

Chicago Water Tower

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 galleries.

Chicago Water Tower
Tribune Tower

Tribune Tower

You can learn about the history of Chicago with a visit to Tribune Tower. Discover the acclaimed art galleries and notable monuments in this vibrant area.

Tribune Tower

Activities

2 Hour Magnificent Chicago Tour with Photos

2 Hour Magnificent Chicago Tour with Photos and Popcorn

NZ$58
per adult
2 Hour Magnificent Chicago Tour with Photos and Popcorn
Harry Potter Shop Chicago: Confectionary Collection

Harry Potter Shop Chicago: Confectionary Collection

NZ$65
per adult
Harry Potter Shop Chicago: Confectionary Collection
Harry Potter Shop Chicago: Magical Brew Bundle

Harry Potter Shop Chicago: Magical Brew Bundle

NZ$125
per adult
Harry Potter Shop Chicago: Magical Brew Bundle
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.