Northwest Side Vacation Packages 2026 from $198

Northwest Side flight + hotel vacation packages

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

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$198

per person

Mar 22 - Mar 24

found 2 days 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

Downtown Chicago

Save 100% on your flight

$502

per person

Mar 22 - Mar 27

found 2 days 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.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$474

per person

Mar 22 - Mar 27

found 2 days 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 free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$388

per person

Mar 22 - Mar 27

found 2 days ago

Roundtrip flight included

Atlanta (ATL) 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.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$453

per person

Mar 22 - Mar 27

found 2 days 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.

Top Northwest Side hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$114 total

Jan 19 - Jan 20

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.

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.

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$94 total

Jan 25 - Jan 26

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.

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$126 total

Jan 20 - Jan 21

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.

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$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.

River Hotel

75 East Wacker Drive Chicago IL

Free Cancellation

Reserve now, pay when you stay

$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. Express check-in, express check-out, and dry cleaning are also on offer.

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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 $198, 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.