Oak Street Vacation Deals: Oak Street, Downtown Chicago Vacations

Oak Street vacation package deals

Prices and availability subject to change. Additional terms may apply.

JW Marriott Chicago

Downtown Chicago

Save 100% on your flight

per person

Jun 6 - Jun 9

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 business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

per person

Jun 6 - Jun 9

Roundtrip flight included

Atlanta (ATL) 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.

Chicago Marriott Downtown Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Jul 11 - Jul 15

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This smoke-free 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 valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a terrace are also provided.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Jun 6 - Jun 9

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.

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Save 100% on your flight

per person

Jun 6 - Jun 9

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.

Aloft Chicago Downtown River North

Downtown Chicago

Save 100% on your flight

per person

Jul 3 - Jul 6

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and a computer station are also offered.

Frequently asked questions

How much are vacation packages to Oak Street?

The perfect $317 package deal is available for your upcoming visit to Oak Street. Why not let Travelocity take the worry out of organizing your vacation? The great thing about bundling your flights and hotel is that it will save you both time and money. It’s win-win!

Where can I get the best vacation package deals for Oak Street?

Travelocity has everything you need to score a sensational Oak Street package deal. Select from as many as 400 air carriers and 1,000,000 properties worldwide and create a travel itinerary that’s right for you. With this amount of choice at your fingertips, now’s the time to book your next great adventure.

Why should I book my Oak Street vacation bundle with Travelocity?

Whether you’re searching for the ultimate unplugged vacation or you crave the hustle and bustle of a towering metropolis, booking everything with Travelocity saves you time, hassle and money. No need to search through hundreds of different websites for the best deal — our Price Match Guarantee ensures you’ll always score the lowest possible price, and our team of customer service experts are available 24/7 should you need anything at all.

Top Oak Street hotel deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$127

per night

Apr 29 - Apr 30

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.

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$160

per night

Apr 28 - Apr 29

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free 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.

Eurostars Magnificent Mile

660 North State Street, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$170

per night

Apr 28 - Apr 29

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.