Deals on vacations and trips to Northwest Side

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Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $1,049, price is now $694 per person
$694
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,341, price is now $791 per person
$791
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, 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 24-hour gym, bar/lounge, and laundry facilities.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,225, price is now $782 per person
$782
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,660, price is now $1,076 per person
$1,076
per person
Nov 12 - Nov 16
found 1 day ago
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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,107, price is now $730 per person
$730
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Dry cleaning, luggage storage, and wedding services are also on offer.

Top Northwest Side 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
$107 nightly
The price is $127 total per night
$127 total
Nov 2 - Nov 3
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
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$161 nightly
The price is $191 total per night
$191 total
Oct 25 - Oct 26
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
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
$143 nightly
The price is $170 total per night
$170 total
Nov 1 - Nov 2
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
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$151 nightly
The price is $179 total per night
$179 total
Nov 1 - Nov 2
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
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $171 total per night
$171 total
Nov 1 - Nov 2
Total with taxes and fees
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Spa
Free WiFi
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$193 nightly
The price is $227 total per night
$227 total
Oct 30 - Oct 31
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 Northwest Side attractions

Portage Park

After visiting Portage Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
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Frequently asked questions

How much are vacation packages to Northwest Side?
Starting from as low as $694, hotel and flight packages are an excellent way to make your budget stretch further. Northwest Side, here you come!
Where can I get the best vacation package deals for Northwest Side?
You can grab sensational Northwest Side package deals with Travelocity. Mix and match from 400 air carriers and 1,000,000 worldwide properties and turn those travel dreams into a reality.
Why should I purchase my Northwest Side vacation package with Travelocity?
With top-notch service, 24/7 customer support and some of the most idyllic escapes around, you'll never wander alone. And if you find a cheaper price, we'll match it. That's our Price Match Guarantee.
Can I save money on my Northwest Side car rental if I book it with hotels and flights?
You sure can with our Northwest Side vacation packages. With one of these, there are tons of ways to stretch your travel budget further. Combine any two or more car, flight, hotel and tour bookings and watch your savings grow. With a rental car, all the main sights in and around Northwest Side are a fun road trip away.
Which airport is best for Northwest Side?
O'Hare Intl. Airport (ORD) is a popular choice for many travelers to Northwest Side. But depending on your schedule, Midway Intl. Airport (MDW) or Lewis University Airport (LOT) could be better options.
What is there to do in Northwest Side?
A diverse and inspiring destination, Northwest Side is home to some wonderful sights and attractions. Portage Park and Walt Disney House are among the local highlights.

Photos of local treasures

Browse Northwest Side vacation photos for more inspiration

A curved pathway with a metal fence, flowering trees, and a street lamp.
The Chicago Theatre with a prominent marquee displaying movie titles.
A city skyline with several high-rise buildings, including a prominent glass skyscraper and a building with a spire.

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