Downtown Chicago Vacation Packages 2025/2026 from $279

Downtown Chicago flight + hotel vacation packages

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

HYATT house Chicago/Schaumburg

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a sauna. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Holiday Inn Chicago O'Hare – Rosemont by IHG

O'Hare

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Self parking, a coffee shop, and a grocery/convenience store are also offered.

Hilton Chicago O'Hare Airport

O'Hare

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 29 - Sep 2

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

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 indoor pool, bar/lounge, and laundry facilities.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Aug 20 - Aug 24

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.

Top Downtown Chicago hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$168 total

Aug 5 - Aug 6

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

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

Free Cancellation

$260 nightly

$300 total

Jul 7 - Jul 8

Total includes taxes and fees

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

Pool

Spa

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$186 total

Jul 10 - Jul 11

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

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$193 nightly

$227 total

Jul 10 - Jul 11

Total includes 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

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$159 total

Jul 7 - Jul 8

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 Whitehall Hotel, BW Premier Collection

105 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$169 total

Jul 7 - Jul 8

Total includes taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Breakfast included

Pet friendly

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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?

$279 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.