Downtown Chicago Holidays

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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

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$304 per night from 22 Sept to 23 Sept
NZ$304
22 Sept - 23 Sept
includes taxes & fees
8.2/10 Very Good! (2,922 reviews)
"Cafe was convenient"

Reviewed on 19 Sept 2025

Warwick Allerton - 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
7.8/10 Good! (9,228 reviews)
"Hotel is older, but very well maintained."

Reviewed on 19 Sept 2025

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Congress Plaza Hotel
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$312 per night from 22 Sept to 23 Sept
NZ$312
22 Sept - 23 Sept
includes taxes & fees
9.2/10 Wonderful! (3,815 reviews)
"Please try to restock luggage tag bands"

Reviewed on 17 Sept 2025

citizenM Chicago Downtown
See all 1,666 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 . 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

4.5/5(64 reviews)

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

4.5/5(73 reviews)

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

Millennium Park
Grant Park

Grant Park

4.5/5(47 reviews)

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

River tour boat in Chicago

Architecture River Tour

NZ$83
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$76
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

NZ$76
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.