Magnificent Mile Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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.
  • Jul 14 - Jul 26

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    12 nights
    4.0 star property
    8.2/10 - Very good (2,778 reviews)
    "Hotel Felix was in a fantastic location. The staff were very friendly. Our room on the 9th floor with 2 double beds was small, with only a mini fridge. The curtains were old and difficult to open and close. The WiFi would drop or was very slow. The television also provided issues, turning off or to the starting screen, multiple times. The hotel offered only coffee/tea and fresh fruit until 9am. The staff made our stay more enjoyable."
    Reviewed June 8, 2026
    Return Auckland (AKL) - Chicago (ORD)
    AKL - ORD2 stops ORD - AKL2 stops
    NZ$7,339
    NZ$5,025
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Jul 14 - Jul 26

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    12 nights
    4.0 star property
    9.2/10 - Wonderful (493 reviews)
    "Fully equipmet"
    Reviewed June 2, 2026
    Return Auckland (AKL) - Chicago (ORD)
    AKL - ORD2 stops ORD - AKL2 stops
    Save 100% on your flight
    NZ$8,374
    NZ$5,408
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Jul 14 - Jul 26

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    12 nights
    4.5 star property
    9.4/10 - Exceptional (3,735 reviews)
    "We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages."
    Reviewed June 7, 2026
    Return Auckland (AKL) - Chicago (ORD)
    AKL - ORD2 stops ORD - AKL2 stops
    Save 100% on your flight
    NZ$10,218
    NZ$6,821
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Jul 14 - Jul 26

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    12 nights
    4.0 star property
    9.4/10 - Exceptional (2,534 reviews)
    "This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually."
    Reviewed June 8, 2026
    Return Auckland (AKL) - Chicago (ORD)
    AKL - ORD2 stops ORD - AKL2 stops
    Save 100% on your flight
    NZ$7,904
    NZ$5,443
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Jul 14 - Jul 26

    Omni Chicago Hotel + Flight

    Downtown Chicago
    12 nights
    4.5 star property
    9.2/10 - Wonderful (1,797 reviews)
    "beautiful room city view excellent location quiet and comfortable"
    Reviewed June 9, 2026
    Return Auckland (AKL) - Chicago (ORD)
    AKL - ORD2 stops ORD - AKL2 stops
    NZ$7,911
    NZ$5,558
    per traveller
    found 1 day ago
    Omni Chicago Hotel

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

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
Fully refundable
The price is NZ$459 per night from 1 July to 2 July
NZ$459
1 July - 2 July
includes taxes & fees
9.2/10 Wonderful! (3,089 reviews)
"Everything with this hotel stay went smoothly, from the valet parking, easy check-in, staff bringing luggage to our room to the most comfortable bed, spacious room and bathroom, and so convenient to everything in downtown Chicago. Loved our visit and would definitely stay again!"

Reviewed on 8 June 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 NZ$381 per night from 7 July to 8 July
NZ$381
7 July - 8 July
includes taxes & fees
8.8/10 Excellent! (1,148 reviews)
"Stay was amazing, local to everything"

Reviewed on 6 June 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 NZ$278 per night from 29 June to 30 June
NZ$278
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,226 reviews)
"Walls are very thin and could here the room next to ours TV all night long."

Reviewed on 9 June 2026

Congress Plaza Hotel
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 . 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

Activities

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.