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 hotel + flight trips 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 Rp1.364.968 per night from 26 Nov to 27 Nov
Rp1.364.968
Rp1.602.336 total
includes taxes & fees
26 Nov - 27 Nov
7.8/10 Good! (8,134 reviews)
"I thought the staff was really helpful. I wasn’t a fan of the parking situation but the garage next door was nice to deal with. They just kept calling with stipulations like you can’t come and go with the car easily and because of concerts we wouldn’t have access at times, that kind of thing. It ..."

Reviewed on 20 Nov 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is Rp1.583.531 per night from 23 Dec to 24 Dec
Rp1.583.531
Rp1.858.909 total
includes taxes & fees
23 Dec - 24 Dec
8.6/10 Excellent! (3,548 reviews)
"I loved the view from my room! I loved that it is right in the middle of Downtown!!! I would stay here again."

Reviewed on 21 Nov 2024

River Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is Rp2.286.000 per night from 16 Dec to 17 Dec
Rp2.286.000
Rp3.080.411 total
includes taxes & fees
16 Dec - 17 Dec
8.6/10 Excellent! (1,004 reviews)
"This is in a fancy part of town, across from the Hancock bldg. There are tons of great restaurants. The shops are… also fancy, translated - mostly for window shopping. It would be awesome if they had 2 people serving coffee in the morning because the line is long."

Reviewed on 21 Nov 2024

The Westin Michigan Avenue Chicago
See all 4,877 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?
Starting from as low as , you can handcraft your own Chicago package the way you want. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Chicago?
Find flights that fit in with your schedule, add a hotel to your booking and watch how much you save with a Chicago holiday package. It’s as easy as that! From flights and hotels to activities and rental cars, Expedia is where your cheap getaway begins. And with more than 550 partner airlines and 1,000,000 properties across the globe to pick from, you won’t be short of choice.
Where should I stay in Chicago?
Central Chicago is an excellent place to stay in Chicago. With interesting attractions like Millennium Park and Willis Tower within easy reach, you won’t have to worry about running out of things to do here. Magnificent Mile is another option. This place has plenty to offer travellers, including John Hancock Centre and Chicago Water Tower.
What are the top hotels in Chicago?
Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are some favourite options in the neighbourhood of Central Chicago. If you’d rather stay in the North Side area, consider locking in a room at The Whitehall Hotel or Hyatt Regency Chicago.
How far in advance should I book my Chicago holiday?
While not all air carriers release ticket prices early, you can normally start comparing international flights on Expedia up to 12 months in advance. This is the time you can bag some fantastic deals. If you’re booking last minute, you may still be in luck. Discounted prices occasionally appear a few weeks prior to departure.
What does an Expedia Chicago travel package include?
Hotels, flights and rental cars — we have them well covered. With Expedia, you can shape your Chicago package just how you like it. All you have to do is work out exactly what you need. Once you’ve made your booking, you can add on fun things like tours and activities. The more you bundle, the greater your savings!
What should I know before booking a Chicago travel package?
We already have low prices. However, you’ll pick up even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you’ll always get transparent pricing and a huge range of choice.
Can I choose my airline with a Chicago Expedia holiday package?
Yes, of course. We have more than 550 partner airlines globally, so fly with the carrier that fits your budget and travel needs.
If I'm not able to travel, can I cancel my Chicago holiday package?
We totally get that life sometimes gets in the way of your plans. If you’ve booked a Chicago holiday package and have to amend or cancel it, we’re here to help. We suggest visiting 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 or change your itinerary at no cost. If it’s been longer than 24 hours, your airline, hotel or car rental company may charge a fee.

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

Rp603.688
Per adult
94% of travellers recommend
Flyover in Chicago
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

Rp706.393
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

Rp774.175
Per adult
94% of travellers recommend
Architecture River Tour
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.