Downtown Chicago Vacation Packages 2025/2026 from $528

Downtown Chicago flight + hotel vacation packages

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

Hampton Inn & Suites Chicago Medical District UIC

Near West Side

$528

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.

Hotel Riu Plaza Chicago

Downtown Chicago

$577

per person

Oct 24 - Oct 27

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.

The Emily Hotel

Downtown Chicago

$1,075

per person

Oct 22 - Oct 29

found 1 day 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.

Trump International Hotel & Tower Chicago

Downtown Chicago

$1,146

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Hyatt Centric Chicago Magnificent Mile

Downtown Chicago

Save 100% on your flight

$968

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.

Top Downtown Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$210 total

Sep 22 - Sep 23

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.

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$216 total

Sep 22 - Sep 23

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 Garden Inn Chicago Downtown/Magnificent Mile

10 E Grand Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$179 total

Oct 2 - Oct 3

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. Express check-out, luggage storage, and concierge services are also on offer.

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$214 total

Sep 22 - Sep 23

Total with taxes and fees

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

Free WiFi

Restaurant

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$189 total

Sep 22 - Sep 23

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.

Freehand Chicago

19 East Ohio Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$141 total

Sep 22 - Sep 23

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.

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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

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

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

Millennium Park

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?

$528 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.