Northwest Side Vacation Packages 2026 from $537

Northwest Side flight + hotel vacation packages

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

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$537

per person

May 7 - May 11

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa, 2 restaurants, and a gym are all featured at this luxury hotel. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi. A business center, a terrace, and dry cleaning are also on offer.

Level Chicago – Old Town

Downtown Chicago

$806

per person

Jun 4 - Jun 7

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) 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.

Warwick Allerton - Chicago

Downtown Chicago

Save 100% on your flight

$1,040

per person

Jun 3 - Jun 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. WiFi in public areas is free.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$1,052

per person

May 7 - May 11

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

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.

Hotel Riu Plaza Chicago

Downtown Chicago

$745

per person

Jun 19 - Jun 21

found 1 day ago

Roundtrip flight included

Nashville (BNA) 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.

Top Northwest Side hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$116 nightly

$136 total

Apr 5 - Apr 6

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

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

$156 nightly

$183 total

Apr 6 - Apr 7

Total with taxes and fees

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.

Breakfast included

Free WiFi

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

$130 nightly

$153 total

Apr 5 - Apr 6

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

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$143 total

Apr 6 - Apr 7

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.

Pool

Pet friendly

Aloft Chicago Mag Mile

243 E. Ontario Chicago IL

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$116 total

Mar 25 - Mar 26

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Valet parking, a business center, and a snack bar/deli are also offered.

Pool

Pet friendly

Hyatt Regency Chicago

151 East Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$200 nightly

$235 total

Apr 5 - Apr 6

Total with taxes and fees

This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and express check-in are also on offer.

Free WiFi

Restaurant

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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

Walt Disney House

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

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.

Horner Park Dog Park

Horner Park Dog Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music while you're in the area.

Frequently asked questions

How much are vacation packages to Northwest Side?

Starting from as low as $537, 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.