Deals on vacations and trips to Northwest Side

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Northwest Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Downtown Chicago
Save 100% on your flight
Price was $583, price is now $339 per person
$339
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a coffee shop, and free WiFi in public areas. Express check-out, luggage storage, and free newspapers are also on offer.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was $4,716, price is now $2,731 per person
$2,731
per person
Sep 13 - Sep 19
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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,089, price is now $633 per person
$633
per person
Sep 6 - Sep 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $990, price is now $610 per person
$610
per person
Sep 6 - Sep 10
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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $996, price is now $622 per person
$622
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

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
$157 nightly
The price is $186 total per night
$186 total
Sep 1 - Sep 2
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
$152 nightly
The price is $181 total per night
$181 total
Aug 23 - Aug 24
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
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $193 total per night
$193 total
Aug 30 - Aug 31
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 business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and limo/town car service are also offered.
Free airport shuttle
Pet friendly
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$222 nightly
The price is $264 total per night
$264 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, conference space, and valet parking. Self parking, a lobby fireplace, and luggage storage are also offered.
Pet friendly
Free WiFi
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$251 nightly
The price is $298 total per night
$298 total
Aug 9 - Aug 10
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. There's in-room fitness on site, and concierge services and wedding services are also offered.
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
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $181 total per night
$181 total
Aug 23 - Aug 24
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 8 conference rooms, free WiFi in public areas, and express check-out. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.
Pet friendly
Free WiFi
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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.
See properties

Frequently asked questions

How much are vacation packages to Northwest Side?
Starting from as low as $339, 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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