Downtown Chicago Vacation Packages 2025 from $430

Downtown Chicago flight + hotel vacation packages

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

DoubleTree by Hilton Chicago Schaumburg

Save 100% on your flight

per person

Aug 6 - Aug 13

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy free perks like free self parking and an area shuttle.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 17 - Jul 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Save 100% on your flight

per person

Jul 17 - Jul 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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.

Hilton Garden Inn Naperville/Warrenville

Save 100% on your flight

per person

Aug 6 - Aug 13

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and a grocery/convenience store are also offered.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Jul 17 - Jul 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli 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

$127 nightly

$150 total

Jul 1 - Jul 2

Total includes 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

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$157 total

Jul 1 - Jul 2

Total includes 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

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$198 total

Jun 30 - Jul 1

Total includes 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 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

Spa

Pet friendly

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$163 nightly

$192 total

Jun 30 - Jul 1

Total includes 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

Fairmont Chicago at Millennium Park

200 North Columbus Drive, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$231 nightly

$271 total

Jun 29 - Jun 30

Total includes taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Spa

Pet friendly

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$166 nightly

$195 total

Jun 5 - Jun 6

Total includes 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-in, and valet parking. A coffee shop, a snack bar/deli, and a lobby fireplace are also on offer.

Pet friendly

Free WiFi

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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

Navy Pier

4.5/5(4,870 reviews)

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

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.

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?

$430 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.