Northwest Side Vacation Packages 2026 from $506

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

$506

per person

Aug 8 - Aug 12

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 Fulton Market

Downtown Chicago

Save 100% on your flight

$682

per person

Aug 19 - Aug 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$758

per person

Aug 19 - Aug 23

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.

Level Chicago - River North

Downtown Chicago

Save 100% on your flight

$683

per person

Aug 19 - Aug 23

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.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$583

per person

Aug 8 - Aug 12

found 1 day 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.

Top Northwest Side hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$162 total

Jun 29 - Jun 30

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

Hyatt Regency O'Hare Chicago

9300 Bryn Mawr Ave Rosemont IL

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$154 total

Jun 28 - Jun 29

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 Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Free Cancellation

$154 nightly

$183 total

Jun 28 - Jun 29

Total with taxes and fees

This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Business travelers can take advantage of the free WiFi in public areas. Self parking, express check-out, and luggage storage are also offered.

Pet friendly

Free WiFi

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free Cancellation

Reserve now, pay when you stay

$162 nightly

$192 total

Jun 29 - Jun 30

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

Hotel Felix River North/Magnificent Mile

111 W Huron St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$174 nightly

$207 total

Jun 30 - Jul 1

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.

Pet friendly

Free WiFi

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave Chicago IL

Free Cancellation

$217 nightly

$259 total

Jul 6 - Jul 7

Total with taxes and fees

This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the sauna and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Pool

Spa

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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 theater scene and entertainment choices in this vibrant area.

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 $506, 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.