Deals on vacations and trips to Downtown Chicago

Choose two or more items and save on your trip:

Downtown Chicago flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
Kenwood
Save 100% on your flight
Price was $622, price is now $389 per person
$389
per person
Nov 26 - Dec 1
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Free self parking is available and the hotel's multilingual staff can provide around-the-clock assistance. WiFi in public areas is free. Luggage storage is also provided.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $946, price is now $575 per person
$575
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $636, price is now $391 per person
$391
per person
Nov 26 - Dec 1
found 1 day ago
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, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
Stay One Chicago

Stay One Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,727, price is now $1,088 per person
$1,088
per person
Nov 26 - Dec 1
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and A 24-hour gym. Enjoy the seasonal outdoor pool and perks like free WiFi. You'll appreciate the hot tub, poolside bar, and coffee shop.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $963, price is now $609 per person
$609
per person
Nov 26 - Dec 1
found 1 day ago
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, free WiFi in public areas, and valet parking. A library, express check-in, and express check-out are also on offer.

Top Downtown Chicago hotels deals

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $213 total per night
$213 total
Sep 27 - Sep 28
Total with taxes and fees
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.
Pet friendly
Free WiFi
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
$201 nightly
The price is $239 total per night
$239 total
Sep 27 - Sep 28
Total with taxes and fees
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.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $213 total per night
$213 total
Oct 13 - Oct 14
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.
Pet friendly
Free WiFi
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$195 nightly
The price is $231 total per night
$231 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and valet parking. Enjoy the free continental breakfast each morning. Express check-in, express check-out, and a computer station are also on offer.
Breakfast included
Pet friendly
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $172 total per night
$172 total
Sep 27 - Sep 28
Total with taxes and fees
This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.
Pet friendly
Free WiFi
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$236 nightly
The price is $281 total per night
$281 total
Oct 12 - Oct 13
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Pool
Hot Tub
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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.

Stay near popular Downtown Chicago attractions

A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
See properties

Frequently asked questions

How much are vacation packages to Downtown Chicago?
$389 is all you need to spend for a wonderful vacation in Downtown Chicago. Bundle your flights and hotel into a vacation package with Travelocity and see the savings grow. With prices as good as these, you'll want to start packing your suitcase now!
Where can I get the best vacation package deals for Downtown Chicago?
For an excellent Downtown Chicago package deal, book with Travelocity. Take your pick from as many as 400 airlines and 1,000,000 worldwide properties to create your dream adventure — it's really that easy.
Why should I purchase my Downtown Chicago vacation bundle via Travelocity?
Because life is one amazing journey, and we offer everything you need to help you along the way. With our top-notch service and Price Match Guarantee, you can book with confidence. What's more, you can rest easy while you're away knowing we're here for you with our round-the-clock support.
Can I save money on my Downtown Chicago car rental if I combine it with a hotel or flight?
Sure can. And our Downtown Chicago vacation packages are the best way to do it. In just a few clicks you can save money as well as time by booking everything in one place. Collect the keys to your rental car and feel the freedom of the open road. Looking for things to do? Add a few tours to your package and make savings on those too.
Which airport is best for Downtown Chicago?
O'Hare Intl. Airport (ORD) is where many people choose to touch down. Depending on what you're hoping to do in Downtown Chicago, Midway Intl. Airport (MDW) and Lewis University Airport (LOT) are other choices for you to look into.
What is there to do in Downtown Chicago?
You'll be happy to know Downtown Chicago is overflowing with incredible photo opportunities, however Millennium Park and Art Institute of Chicago are two you shouldn't miss.

Photos of local treasures

Browse Downtown Chicago vacation photos for more inspiration

A busy city street with tall buildings, a bus, and cars.
A busy urban sidewalk with pedestrians, a Marriott hotel, and lush greenery.
A cityscape with tall skyscrapers and a historic tower.
Michael Jordan's Steak House with ornate metalwork and a sign for the bar and salon.
A street sign for State St. and a building with an 'Oriental' sign.

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