Downtown Chicago Holidays from NZ$2,395

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Top Holiday Package Deals in Downtown Chicago

Price found within the past 48 hours. Click for updated prices.
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 NZ$2,901, price is now NZ$2,395 per person
NZ$2,395
per person
21 Jan - 26 Jan
found 12 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
The room was amazing, views were amazing, staff is very friendly and helpful, I’m definitely coming back here for sure .

Reviewed on 20 Dec 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was NZ$4,972, price is now NZ$3,868 per person
NZ$3,868
per person
21 Jan - 26 Jan
found 12 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel!

Reviewed on 19 Dec 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$3,112, price is now NZ$2,499 per person
NZ$2,499
per person
21 Jan - 26 Jan
found 12 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Overall good experience. My room was not cleaned one of the nights because the maid didn’t come until late but we were already in our room. Also, the $25/night resort fee was not properly explained to me, didn’t make much sense at all honestly. Property is nice and in a great location but i wouldn’t stay here again

Reviewed on 19 Dec 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was NZ$3,198, price is now NZ$2,579 per person
NZ$2,579
per person
21 Jan - 26 Jan
found 12 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
9.2/10 Wonderful! (326 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on 18 Dec 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was NZ$3,037, price is now NZ$2,511 per person
NZ$2,511
per person
21 Jan - 26 Jan
found 12 hours ago
Return flight included
Wellington (WLG) to Chicago (ORD)
8.4/10 Very Good! (2,301 reviews)
Great stay, lovely hotel. Great staff all around, Hannah upgraded our room to a 2 bathroom 2 bed with no charge after seeing we had a 4 party guest reservation. Definitely will be staying here again

Reviewed on 20 Dec 2025

Our guide on where to stay in Downtown Chicago

Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago
Magnificent Mile - River North

Magnificent Mile

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

Find hotels in Magnificent Mile

Our pick of the best Downtown Chicago Hotel Deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$182 per night from 5 Jan to 6 Jan
NZ$182
5 Jan - 6 Jan 2026
includes taxes & fees
8.8/10 Excellent! (3,507 reviews)
Clean Room

Reviewed on 18 Dec 2025

Hilton Chicago/Magnificent Mile Suites
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,130 reviews)
Clean room, attentive staff, great lounge!

Reviewed on 15 Dec 2025

Get rates
Silversmith Hotel Chicago Downtown
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$169 per night from 21 Dec to 22 Dec
NZ$169
21 Dec - 22 Dec
includes taxes & fees
8.6/10 Excellent! (2,003 reviews)
Easy check in/check out process. Staff was very friendly and helpful. Hotel is conveniently located for walking to shopping, food, and sightseeing

Reviewed on 17 Dec 2025

Club Quarters Hotel Wacker at Michigan, Chicago
See all 1,718 properties in Downtown Chicago
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 Downtown Chicago holiday package cost?
Go from looking to booking with our Downtown Chicago holiday packages, which start from just NZ$2,395. Handpick the hotels and flights that suit your travel style. Then, add on a couple of tours or activities for an amazing adventure.
How do I get a cheap travel package to Downtown Chicago?
Bundle your bookings with Expedia to save big on your next trip. With more than 550 partner airlines and 1 000 000 hotels across the world, your Downtown Chicago holiday package can be tailored exactly to suit your budget. With all that extra money, why not include one or two fun tours and activities? It's an easy way to unlock even more savings. The holiday you've always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago holiday?
While not all airlines advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is the time you'll score some incredible deals. If you've left things to the last minute, you could still be in luck. Discounted prices occasionally emerge a few weeks before departure.
What does an Expedia Downtown Chicago travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Downtown Chicago trip. You can also add on fun things like activities and tours once you've made your booking. You're in charge! When you combine your bookings with Expedia, you'll score discounts you won't find elsewhere.
What should I know before booking a Downtown Chicago travel package?
Our prices are always low. However, you'll pick up even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Downtown Chicago Expedia holiday package?
Yes — that's the beauty of an Expedia holiday package. You're in charge! We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Downtown Chicago trip.
If I'm not able to travel, can I cancel my Downtown Chicago holiday package?
You can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Downtown Chicago holiday package. You may be able to change or cancel your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Downtown Chicago

Navy Pier

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

See mind-bending sculptures, a musically-inspired lawn and giant water fountains that double-up as video screens.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Activities

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$70
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

NZ$76
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
Art Institute of Chicago

Art Institute of Chicago

NZ$69
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago

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