Downtown Chicago Vacations

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to $580 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Downtown Chicago Vacation

Reserving a Downtown Chicago vacation package is a great way to get to know this unique neighborhood. From its must-visit places to its lesser-known delights, you'll be sure to uncover something new. Some leading nearby attractions to see during your trip to Downtown Chicago include Millennium Park, Willis Tower and Art Institute of Chicago. Whatever your travel plans or the size of your budget, booking your dream Downtown Chicago vacation is a cinch with Expedia.

The Latest Downtown Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

2 out of 5
O'Hare
Save 100% on your flight
per person
Sep 26 - Sep 30
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,469 reviews)
If it wasn’t for the super friendly and helpful front desk person I would definitely have been a bit concerned for my stay. I don’t typically end up at airport hotels (this was due to a flight cancellation) and the area was a bit desolate looking. But my arrival was so easy and welcoming! I wish I had gotten her name but what a great energy that really made me feel comfortable and at ease. The rooms themselves we ok, a bit dated, but provided the amenities I needed for the night.

Reviewed on Jul 26, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,040 reviews)
The staff is amazing from the front door, front desk, bar, restaurant, coffee shop and cleaning staff. They always had a smile and were ready to provide service or advice.

Reviewed on Jul 25, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (231 reviews)
Loved everything about this property, especially the amenities!

Reviewed on Jul 25, 2024

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,212 reviews)
Rooms are clean but very small. Especially the bathrooms

Reviewed on Jul 23, 2024

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (710 reviews)
great location, on site restaurants/bars were nice

Reviewed on Jul 23, 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

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

Find hotel + flight trips in Magnificent Mile

Downtown Chicago Hotel Deals

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 $179 per night from Aug 26 to Aug 27
$179
includes taxes & fees
$152 per night
Aug 26 - Aug 27
7.6/10 Good! (7,478 reviews)
"location"

Reviewed on Jul 26, 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 $175 per night from Aug 26 to Aug 27
$175
includes taxes & fees
$149 per night
Aug 26 - Aug 27
8.6/10 Excellent! (3,150 reviews)
"The location is fantastic! I would consider staying here again. However, I made a reservation for River Hotel and fully expected a view of the Chicago River. But my room was in Club Quarters and my view was a wall. Felt a little mislead. Next time, I will ask more questions about the room ..."

Reviewed on Jul 26, 2024

River Hotel
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $243 per night from Aug 23 to Aug 24
$243
includes taxes & fees
$210 per night
Aug 23 - Aug 24
8/10 Very Good! (1,369 reviews)
"Very nice hotel"

Reviewed on Jul 26, 2024

Palmer House a Hilton Hotel
See all 1,598 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Downtown Chicago vacation package cost?
Go from looking to booking with our Downtown Chicago vacation packages, which start from just $244. 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 vacation 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 vacation you’ve always dreamed of in Downtown Chicago is much closer than you thought!
How far in advance should I book my Downtown Chicago vacation?
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 vacation package?
Yes — that’s the beauty of an Expedia vacation 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 vacation 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 vacation 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.

Discover the most popular places to visit in Downtown Chicago

Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier
Image for Michigan Avenue

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Image for Grant Park

Grant Park

4.5/5(3,318 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 Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
96% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Seadog Lakefront Speedboat Tour

Chicago Seadog Lakefront Speedboat Tour

$42
Per adult
80% of travellers recommend
Chicago Seadog Lakefront Speedboat Tour
Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$188
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.