Chicago Holidays

    Plan, book, travel with confidence
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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Chicago Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
per person
23 Dec - 30 Dec
found 17 hours ago
Return direct flight included
Milan (MXP) to Chicago (ORD)
7.8/10 Good! (7,993 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 was convenient for transportation, walking, food and other conveniences which was nice. The room was really nice but the air conditioning/heat kept getting stuck on high blast and was too warm for our liking even when we tried to adjust it, made for difficult sleeping. Price was good and fair compared to other sites in the area.

Reviewed on 20 Nov,2024

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
23 Dec - 30 Dec
found 17 hours ago
Return direct flight included
Milan (MXP) to Chicago (ORD)
8.2/10 Very Good! (2,454 reviews)
Stay was great, hated parking fees

Reviewed on 20 Nov,2024

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
Downtown Chicago
per person
23 Dec - 30 Dec
found 17 hours ago
Return direct flight included
Milan (MXP) to Chicago (ORD)
8.8/10 Excellent! (1,730 reviews)
Staff was excellent, room is comfortable

Reviewed on 17 Nov,2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 S$134 per night from 25 Nov to 26 Nov
S$134
includes taxes & fees
25 Nov - 26 Nov
7.8/10 Good! (8,136 reviews)
"Great staff made the stay worth it. Will go back when I return to Chicago."

Reviewed on 19 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 S$165 per night from 22 Dec to 23 Dec
S$165
includes taxes & fees
22 Dec - 23 Dec
8.6/10 Excellent! (3,542 reviews)
"Highly recommend ."

Reviewed on 20 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
Fully refundableReserve now, pay when you stay
The price is S$259 per night from 25 Nov to 26 Nov
S$259
includes taxes & fees
25 Nov - 26 Nov
8.6/10 Excellent! (1,011 reviews)
"The staff was very welcoming. The rooms were clean. Great location and view! Good cocktails!"

Reviewed on 19 Nov,2024

The Westin Michigan Avenue Chicago
See all 4,874 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 S$1,648, 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

McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Millennium Park which includes modern architecture, a city and autumn leaves

Millennium Park

4.5/5(147 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park

What to do in Chicago

Flyover in Chicago

Flyover in Chicago

S$50
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

S$58
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
River tour boat in Chicago

Architecture River Tour

S$71
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.