Deals on vacations and trips to Downtown Chicago

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Downtown Chicago flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 29
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 14 - Jun 17
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 29
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 29
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 17 - Jun 20
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.

Top Downtown Chicago hotel deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $159 per night
$159
per night
May 12 - May 13
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Breakfast available
Parking available
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $125 per night
$125
per night
May 28 - May 29
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking.
Pet friendly
Parking available
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
909 North Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $181 per night
$181
per night
May 13 - May 14
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Pet friendly
Breakfast available
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $159 per night
$159
per night
May 12 - May 13
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $149 per night
$149
per night
May 12 - May 13
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Valet parking, a business center, and a snack bar/deli are also offered.
Pet friendly
Breakfast available
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
Free Cancellation
Reserve now, pay when you stay
The price is $165 per night
$165
per night
May 27 - May 28
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pet friendly
Breakfast included
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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.

Popular places to visit

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 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
Image for Millennium Park

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Frequently asked questions

How much are vacation packages to Downtown Chicago?
Treat yourself to a fulfilling travel experience in Downtown Chicago with a vacation package starting from as low as $462. Booking flights and hotels through Travelocity is so easy. What’s more, our vacation deals will leave you with more savings for plenty of fun activities.
Where can I get the best vacation package deals for Downtown Chicago?
It’s difficult to beat Travelocity when it comes to putting together your Downtown Chicago package deal. There are at least 400 air carriers and 1,000,000 properties worldwide to choose from. Book your vacation now and get ready to cross another destination off your travel bucket list.
Why should I book my Downtown Chicago vacation package with Travelocity?
Travel should be about making cherished memories and leaving all your worries behind — which is why we have a team of experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you’ll always get the best deal available on our impressive range of package deals. So what are you waiting for? There’s no time like the present to lock in the vacation you’ve always dreamed of.
Can I save money on my Downtown Chicago car rental if I book it with hotels and flights?
Bundling your bookings into a Downtown Chicago vacation package will save you a tidy sum. You can bundle a car and flight; a flight, hotel and car; or a car and hotel. You won’t find a better way to discover the greater Downtown Chicago area than with your own set of wheels. You can also add experiences and activities to your Travelocity package.
What is the best time of year to go to Downtown Chicago?
You’ll be able to avoid the tourist crowds and save money in January, September and December, which are the quietest times for tourism. The peak season months of March, May and June are of course busier (and more expensive), but there’ll be more events on around Downtown Chicago. Reserve a hotel in and enjoy more bang for your buck. As a rule, room rates are highest in .
Which airport is best for Downtown Chicago?
For people contemplating visiting Downtown Chicago, the most common airports are O’Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT).
What is there to do in Downtown Chicago?
Downtown Chicago is teeming with terrific photo opportunities, however Millennium Park and Willis Tower are two favorites.