The Loop 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 (2,777 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 (1,798 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 pick of the best The Loop Hotel Deals

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 30 June to 1 July
NZ$278
30 June - 1 July
includes taxes & fees
8/10 Very Good! (10,221 reviews)
"Fantastic room and location."

Reviewed on 9 June 2026

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$510 per night from 2 July to 3 July
NZ$510
2 July - 3 July
includes taxes & fees
8.6/10 Excellent! (2,489 reviews)
"It was good but the rooms need a bit of renovation . The experience from check out to check out was smooth. Breakfast was tasty 😋 will be back soon"

Reviewed on 8 June 2026

Palmer House a Hilton Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is NZ$235 per night from 5 July to 6 July
NZ$235
5 July - 6 July
includes taxes & fees
8.8/10 Excellent! (5,245 reviews)
"Friendly staff, clean room, let us check in early"

Reviewed on 8 June 2026

River 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 The Loop holiday package cost?
Much less than you might think — from as low as , in fact! By bundling flights, hotels and car rentals into your own custom-made package, your The Loop escape is only clicks away.
How do I get a cheap travel package to The Loop?
Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you cash too. A The Loop holiday package makes it easy to organise the perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule will be no sweat. Not only that, we have over 1 000 000 properties globally to select from. Now that's what you call choice. Whatever your budget, Expedia will help show you the world.
Where should I stay in The Loop?
A journey to The Loop isn't over until you've seen McCormick Place and Millennium Park. Look for somewhere to stay within walking distance so you can easily access these impressive tourist attractions.
What are the top hotels in The Loop?
If it's your first time staying in The Loop, make a reservation at Canopy by Hilton Chicago Central Loop or Hilton Garden Inn Chicago Central Loop. Both hotels offer comfy beds and are favourites with many travellers.
How far in advance should I book my The Loop holiday?
To bag rock-bottom prices, book nice and early. Airlines typically advertise flights, along with some of the lowest fares, nearly a year prior to departure. Hotels, car rental and experiences should also be booked well in advance to avoid disappointment. If you were hoping for a last-minute getaway to The Loop, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia The Loop travel package include?
That depends on what you want. If you're travelling solo, you might decide to bundle flights and hotels. Taking the whole family to The Loop? A travel package including flights, hotels and rental cars might suit you better. Expedia gives you the freedom to customize your travel package.
Can I choose my airline with a The Loop Expedia holiday package?
Most definitely. Expedia has over 550 partner airlines to choose from globally. With so many choices, finding the ideal carrier to whisk you away to The Loop will be a snap.
If I'm not able to travel, can I cancel my The Loop holiday package?
We totally understand that life sometimes gets in the way of your plans. If you've booked a The Loop holiday package and need to cancel or change it, we're here to help. We recommend browsing our Customer Service Portal first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel and rebook for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

Discover the most popular places to visit in The Loop

Activities

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