Far North Side Vacation Packages 2026 from $397

Far North Side flight + hotel vacation packages

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

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$397

per person

Jan 29 - Feb 3

found 1 day ago

Roundtrip flight included

Miami (MIA) 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$787

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$588

per person

Mar 13 - Mar 16

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.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$594

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip flight included

Nashville (BNA) 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.

Pendry Chicago

Downtown Chicago

$548

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Top Far North Side hotels deals

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$105 total

Jan 5 - Jan 6, 2026

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

Silversmith Hotel Chicago Downtown

10 S Wabash Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$149 total

Jan 4 - Jan 5, 2026

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 library, express check-in, and express check-out are also on offer.

Free WiFi

Air conditioning

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$174 total

Dec 26 - Dec 27

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.

Pool

Spa

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

Dec 28 - Dec 29

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

Eurostars Magnificent Mile

660 North State Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$113 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Spa

Free WiFi

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$116 total

Jan 6 - Jan 7, 2026

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

Montrose Harbor

Explore the waterfront in Chicago with a trip to Montrose Harbor. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

Explore the Swedish heritage at this unique museum in Lincoln Square that highlights the culture and history of Swedish American immigrants.

Swedish American Museum Center

You can spend an afternoon exploring the galleries in Swedish American Museum Center in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

Aragon Ballroom

4.5/5(9 reviews)

Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Frequently asked questions

How much are vacation packages to Far North Side?

You might be surprised — you can vacation in Far North Side for as little as $397. Let Travelocity save you time and money with our awesome vacation packages. With experiences, hotels and flights all available at our one-stop shop, why wait?

Where can I get the best vacation package deals for Far North Side?

There are fantastic Far North Side package deals waiting for you with Travelocity. Did you know we partner with as many as 400 airlines and 1,000,000 properties worldwide? Remember this the next time you're ready to tick another place off the old bucket list.

Why should I book my Far North Side vacation bundle with Travelocity?

Nothing beats the feeling of knowing you've scored the best deal in town — that's our Price Match Guarantee. Add to that our inspiring range of destinations and 24/7 team of customer service professionals and you've got the blueprint for a stress-free vacation.

Can I save on my Far North Side car rental if I book it with my hotel or flight?

You sure can with our Far North Side vacation packages. With one of these, there are tons of ways to make your hard-earned cash go further. Combine any two or more car, flight, hotel and tour bookings and watch your savings start to pile up. With a rental car, all the main sights around Far North Side are a fun road trip away.

Which airport is best for Far North Side?

O'Hare Intl. Airport (ORD) is a popular choice for many people visiting the region. But depending on what you plan to do, Midway Intl. Airport (MDW) or Lewis University Airport (LOT) could work better for you.

What is there to do in Far North Side?

Far North Side boasts hidden gems around every turn, however ensure you plan a visit to both Lincoln Park and Loyola University Chicago during your stay. These two attractions should be on your to-do list.