Downtown Chicago Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

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

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 ฿4,534 per night from 29 Jun to 30 Jun
฿4,534
฿5,391 total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,143 reviews)
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."

Reviewed on 31 May 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is ฿4,941 per night from 28 Jun to 29 Jun
฿4,941
฿5,874 total
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,499 reviews)
"Everything was great"

Reviewed on 31 May 2026

The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ฿6,144 per night from 30 Jun to 1 Jul
฿6,144
฿8,230 total
30 Jun - 1 Jul
includes taxes & fees
9.4/10 Exceptional! (4,313 reviews)
"Great clean room, staff were so nice!"

Reviewed on 1 Jun 2026

Hotel Riu Plaza Chicago
See all 1,636 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(127 reviews)

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

Navy Pier
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
Chicago Riverwalk

Chicago Riverwalk

4.5/5(29 reviews)

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.

Chicago Riverwalk

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿874
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

฿1,424
per adult
94% of travellers recommend
Skydeck - Willis Tower Admission
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

฿3,569
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
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.