Book Exclusive Downtown Chicago Vacation Packages

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Downtown Chicago flight + hotel packages

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JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Willis Tower and Millennium Park are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 11 - Jul. 14
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Jul. 5 - Jul. 8
Roundtrip non-stop flight included
Ottawa (YOW) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 31 - Aug. 5
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Jul. 11 - Jul. 14
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a nightclub, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.

Top Downtown Chicago hotels 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 CA $206 per night
CA $206
per night
May 13 - May 14
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
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 CA $157 per night
CA $157
per night
May 27 - May 28
Book a stay at this family-friendly hotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and in-room massages. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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 CA $247 per night
CA $247
per night
May 13 - May 14
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Spa
Pet-friendly
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 CA $207 per night
CA $207
per night
May 12 - May 13
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pet-friendly
Parking available
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 CA $204 per night
CA $204
per night
May 12 - May 13
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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 CA $208 per night
CA $208
per night
May 27 - May 28
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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(459 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

Navy Pier
Image for Grant Park

Grant Park

4.5/5(291 reviews)

Explore the great outdoors with a trip to Grant Park, a popular green space in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Grant Park
Image for Millennium Park

Millennium Park

4.5/5(722 reviews)

Explore the great outdoors with a trip to Millennium Park, a popular green space in Chicago. Stroll along the riverfront or visit the notable monuments in this vibrant area.

Millennium Park

Downtown Chicago Vacations

Have more fun, worry less and wander wisely in Downtown Chicago! Get your trip off to a great start by learning a bit about this alluring destination.

About 0.6 miles (1 kilometer) to the northeast of central Chicago, Downtown Chicago is one of the neighborhoods that make this city so appealing.

Chicago is home to some 2,700,000 locals.

Hotels in Downtown Chicago

Finding an ideal place to stay close to Downtown Chicago is simple. There are 122 accommodations to select from, all within walking distance of the center. Reserve your room today and start counting down to your big trip!

If you're wanting a luxury vacation, you'll find no greater place in Downtown Chicago than the Chicago Premier Suites (540 N State Street) or The Peninsula Chicago (108 East Superior Street). If that's not what you're looking for, check out the Trump International Hotel & Tower Chicago (401 N Wabash Ave) or The St. Clair Hotel (162 East Ontario Street). You'll be able to put away some cash and still have an unforgettable vacation.

There's a good selection of accommodations only a walk away from the Art Institute of Chicago. Spend a night or two at The Langham, Chicago or the JW Marriott Chicago and you'll be able to enjoy the neighborhood in all its glory while being right in the middle of all the excitement!

Places to visit in Downtown Chicago

Be sure to recharge your camera before you head to Downtown Chicago, because you'll be virtually around the corner from world-renowned attractions, the Art Institute of Chicago and Willis Tower!

There's plenty to keep you occupied in this buzzing neighborhood. Attractions like Navy Pier and the Chicago Cultural Center are just a brisk walk away.

Even on a drizzly day, it's worthwhile strolling through Millennium Park. Put up your umbrella and soak up the fresh earthy smell. Need more nearby options? Cast your gaze up — way up! John Hancock Center is among the most notable buildings in the local skyline and one that's certainly hard to miss. And there's more. Want to witness a sunrise among some spectacular scenery? Skydeck Ledge boasts astounding views that you won't forget in a hurry.

Where do you fly into for Downtown Chicago?

Arriving at Midway International Airport (MDW)? Walk through the security gates, head out of the terminal and you'll be 9 miles (14 kilometers) to the southwest from the center of Downtown Chicago.