Downtown Chicago Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to ฿4,531 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
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
17 Dec - 20 Dec
found 7 hours ago
Return direct flight included
Bangkok (BKK) to Chicago (ORD)
9/10 Wonderful! (263 reviews)
Service was great, room was neat and very clean. Would stay again!

Reviewed on 4 Oct 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
17 Dec - 20 Dec
found 7 hours ago
Return direct flight included
Bangkok (BKK) to Chicago (ORD)
9.4/10 Exceptional! (1,390 reviews)
3rd time staying there EXCELLENT!!

Reviewed on 4 Nov 2024

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
per person
17 Dec - 20 Dec
found 7 hours ago
Return direct flight included
Bangkok (BKK) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Excellent service, we will be back!

Reviewed on 2 Nov 2024

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
17 Dec - 20 Dec
found 7 hours ago
Return direct flight included
Bangkok (BKK) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Exceeded my expectations. This is my new go-to hotel when in Chicago!

Reviewed on 14 Oct 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
17 Dec - 20 Dec
found 7 hours ago
Return direct flight included
Bangkok (BKK) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
The service at the Langham is impeccable.

Reviewed on 4 Nov 2024

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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

Find hotel + flight trips in Magnificent Mile

Top hotels in Downtown 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 ฿4,622 per night from 7 Nov to 8 Nov
฿4,622
฿5,426 total
includes taxes & fees
7 Nov - 8 Nov
7.8/10 Good! (8,074 reviews)
"Nice older charm"

Reviewed on 2 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 ฿3,947 per night from 24 Nov to 25 Nov
฿3,947
฿4,633 total
includes taxes & fees
24 Nov - 25 Nov
8.6/10 Excellent! (3,537 reviews)
"."

Reviewed on 2 Nov 2024

River Hotel
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is ฿3,991 per night from 24 Nov to 25 Nov
฿3,991
฿4,685 total
includes taxes & fees
24 Nov - 25 Nov
8.2/10 Very Good! (3,178 reviews)
"It was perfect. We will be back."

Reviewed on 3 Nov 2024

Embassy Suites by Hilton Chicago Downtown River North
See all 1,630 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 ฿201,052. 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.

Popular places to visit

Image for Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Image for Millennium Park

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
Image for 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

Things to do

Image for Flyover in Chicago

Flyover in Chicago

฿1,281
Per adult
94% of travellers recommend
Flyover in Chicago
Image for Architecture River Tour

Architecture River Tour

฿1,809
Per adult
94% of travellers recommend
Architecture River Tour
Image for Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

฿1,499
Per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge 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.