Downtown Chicago Vacation Packages 2026 from $179

Downtown Chicago flight + hotel vacation packages

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

Hotel Felix River North/Magnificent Mile

Downtown Chicago

$179

per person

Feb 9 - Feb 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

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.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$552

per person

Feb 13 - Feb 16

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$245

per person

Feb 9 - Feb 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$305

per person

Feb 20 - Feb 23

found 5 hours ago

Roundtrip flight included

Dallas (DAL) 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.

Chicago Marriott Oak Brook

Save 100% on your flight

$338

per person

Mar 4 - Mar 8

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 14 conference rooms, free WiFi in public areas, and express check-in. Free self parking, a coffee shop, and a terrace are also offered.

Top Downtown Chicago hotels deals

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$95 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.

Silversmith Hotel Chicago Downtown

10 S Wabash Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$149 total

Dec 21 - Dec 22

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.

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$100 total

Dec 29 - Dec 30

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.

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$155 total

Dec 21 - Dec 22

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.

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$113 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.

Eurostars Magnificent Mile

660 North State Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$110 total

Jan 13 - Jan 14, 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.

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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

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Frequently asked questions

How much are vacation packages to Downtown Chicago?

$179 is all you need to spend for a wonderful vacation in Downtown Chicago. Bundle your flights and hotel into a vacation package with Travelocity and see the savings grow. With prices as good as these, you'll want to start packing your suitcase now!

Where can I get the best vacation package deals for Downtown Chicago?

For an excellent Downtown Chicago package deal, book with Travelocity. Take your pick from as many as 400 airlines and 1,000,000 worldwide properties to create your dream adventure — it's really that easy.

Why should I purchase my Downtown Chicago vacation bundle via Travelocity?

Because life is one amazing journey, and we offer everything you need to help you along the way. With our top-notch service and Price Match Guarantee, you can book with confidence. What's more, you can rest easy while you're away knowing we're here for you with our round-the-clock support.

Can I save money on my Downtown Chicago car rental if I combine it with a hotel or flight?

Sure can. And our Downtown Chicago vacation packages are the best way to do it. In just a few clicks you can save money as well as time by booking everything in one place. Collect the keys to your rental car and feel the freedom of the open road. Looking for things to do? Add a few tours to your package and make savings on those too.

Which airport is best for Downtown Chicago?

O'Hare Intl. Airport (ORD) is where many people choose to touch down. Depending on what you're hoping to do in Downtown Chicago, Midway Intl. Airport (MDW) and Lewis University Airport (LOT) are other choices for you to look into.

What is there to do in Downtown Chicago?

You'll be happy to know Downtown Chicago is overflowing with incredible photo opportunities, however Millennium Park and Art Institute of Chicago are two you shouldn't miss.