Northwest Side Vacation Packages 2026 from $396

Northwest Side flight + hotel vacation packages

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

Sand Hill On The Lake

Save 100% on your flight

$396

per person

Feb 14 - Feb 18

found 18 hours ago

Roundtrip flight included

Miami (MIA) to Chicago (ORD)

A private beach and a restaurant are featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A virtual front desk are provided for your convenience.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$419

per person

Feb 20 - Feb 23

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Holiday Inn Chicago – Midway Airport S by IHG

West Lawn

Save 100% on your flight

$402

per person

Apr 5 - Apr 10

found 16 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a 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 coffee shop, and a snack bar/deli are also offered.

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

Save 100% on your flight

$416

per person

Apr 8 - Apr 11

found 19 hours ago

Roundtrip flight included

Los Angeles (LAX) 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.

La Banque Hotel

Save 100% on your flight

$432

per person

Feb 22 - Feb 26

found 24 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Top Northwest Side hotels deals

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$182 total

Feb 1 - Feb 2

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

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$105 total

Jan 25 - Jan 26

Total with taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

$88 nightly

$103 total

Jan 30 - Jan 31

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. A snack bar/deli, express check-in, and express check-out are also on offer.

Pet friendly

Free WiFi

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$193 total

Jan 20 - Jan 21

Total with taxes and fees

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 limo/town car service.

Sable at Navy Pier Chicago, Curio Collection by Hilton

900 E Grand Chicago IL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$153 total

Jan 20 - Jan 21

Total with taxes and fees

This 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, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Free WiFi

Restaurant

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$110 total

Jan 21 - Jan 22

Total with taxes and fees

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.

Pool

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

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.

Walt Disney House

Learn about the local history of Chicago when you take a trip to Walt Disney House. Experience the acclaimed art scene and entertainment choices in this vibrant area.

Six Corners

You can browse for the perfect souvenirs at Six Corners during your stay in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Frequently asked questions

How much are vacation packages to Northwest Side?

Starting from as low as $396, 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.