Chicago Holidays

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Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
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

Top hotels in 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 Rp1.502.055 per night from 28 Jan to 29 Jan
Rp1.502.055
Rp1.763.260 total
includes taxes & fees
28 Jan - 29 Jan
7.8/10 Good! (8,426 reviews)
Excellent stay, great rates
"Wonderful, friendly staff. Our room amd view were amazing. Great prices, too!"

Reviewed on 26 Jan 2025

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 Rp1.601.028 per night from 5 Feb to 6 Feb
Rp1.601.028
Rp1.879.672 total
includes taxes & fees
5 Feb - 6 Feb
9.2/10 Wonderful! (2,593 reviews)
"Great stay, easy and convenient."

Reviewed on 24 Jan 2025

citizenM Chicago Downtown
Pendry Chicago
Pendry Chicago
4.5 out of 5
230 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp2.668.380 per night from 9 Feb to 10 Feb
Rp2.668.380
Rp3.796.919 total
includes taxes & fees
9 Feb - 10 Feb
9.2/10 Wonderful! (1,003 reviews)
"Great"

Reviewed on 24 Jan 2025

Pendry Chicago
See all 4,970 properties in 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 Chicago holiday package cost?
You’ll find cheap prices on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Chicago costs.
What are the cheapest months to go to Chicago?
December, January and February are the best times to look for cheap Chicago holiday packages. Opting to travel in quieter periods means you’ll typically find lower prices on accommodation and flights.
How many days is enough for Chicago?
To fully enjoy a Chicago holiday, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue, Chicago Riverwalk and other well-known attractions, on top of experiencing neighbourhoods like Central Chicago and Near North Side. If you’ve got some spare time, include a day trip or tour in your Chicago holiday itinerary.
Is it worth booking a holiday package to Chicago?
Chicago has everything you need for a fantastic trip — views, dining and culture are just the start. Whether you want to visit attractions like Navy Pier and Soldier Field, or take the road less traveled, you’ll find plenty to do on your Chicago holiday.
How to find the best Chicago package deals?
Use Expedia’s filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it’s typically best to lock in your holiday package well in advance.
Is it cheaper to book a Chicago holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You’ll usually score a better deal than booking each component separately. And you’ll still have the freedom to create a customised Chicago holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Chicago?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.
How to plan a trip to Chicago?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chicago.
  2. Set a budget: Factor in costs like flights, transportation and food when working out how much to put aside for your trip to Chicago. Then, choose a property that suits your budget, whether that’s an affordable stay or a swankier getaway.
  3. Work out your trip length: Consider how long you’d like to spend discovering Chicago. Plan your days so you can get to all the attractions and activities you’re interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that’s left is to choose a Chicago holiday package that brings all your bookings together.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park

Grant Park

4.5/5(96 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

What to do in Chicago

Flyover in Chicago

Flyover in Chicago

Rp616.733
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

Rp790.903
per adult
94% of travellers recommend
Architecture River Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

Rp551.378
per adult
Color Factory Chicago Ticket
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.