Downtown Chicago Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Save up to ฿4,531 when you book a flight and hotel together*
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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 hotels in Magnificent Mile

Top hotels in Downtown Chicago

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
Fully refundableReserve now, pay when you stay
The price is ฿4,946 per night from 20 Apr to 21 Apr
฿4,946
฿5,807 total
includes taxes & fees
20 Apr - 21 Apr
8.2/10 Very Good! (3,885 reviews)
"We loved the breakfast staff was great will be returning"

Reviewed on 15 Apr 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿6,008 per night from 19 Apr to 20 Apr
฿6,008
฿8,032 total
includes taxes & fees
19 Apr - 20 Apr
8.8/10 Excellent! (2,060 reviews)
"There was a pile of dirt behind the bed, desk and sofa. All else great!"

Reviewed on 16 Apr 2025

Swissotel - Chicago
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿4,640 per night from 21 Apr to 22 Apr
฿4,640
฿5,446 total
includes taxes & fees
21 Apr - 22 Apr
8.8/10 Excellent! (2,133 reviews)
"Great location in Chicago city"

Reviewed on 16 Apr 2025

Hilton Chicago/Magnificent Mile Suites
See all 1,566 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.

Popular places to visit

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
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
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

Things to do

Flyover in Chicago

Flyover in Chicago

฿1,319
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

฿1,692
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

฿1,522
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.