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Oak Street Vacation Packages

Photo by Eleonora Bertacchi

3-4 Night Vacations in Oak Street

Pendry Chicago
Swissotel - Chicago
Fairmont Chicago at Millennium Park Gold Experience
Trump International Hotel & Tower Chicago
Prices and availability subject to change. Additional terms may apply.

Oak Street Last Minute Hotel Deals

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy WiFi, a 24-hour fitness center, and valet parking. Our guests praise the helpful staff and the clean ...
Warwick Allerton - Chicago
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
River Hotel
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
The Westin Michigan Avenue Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
Thompson Chicago, by Hyatt
Thompson Chicago, by Hyatt
4.5 out of 5
21 East Bellevue, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a fitness center, and valet parking. Our guests praise the bar and the helpful staff in our reviews. ...
Thompson Chicago, by Hyatt
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy WiFi, a fitness center, and valet parking. Our guests praise the pool and the helpful staff in ...
Hilton Chicago/Magnificent Mile Suites
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Eurostars Magnificent Mile
W Chicago - Lakeshore
W Chicago - Lakeshore
4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast, WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
W Chicago - Lakeshore
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.

Book the perfect getaway to Oak Street

With Hotwire, booking your next trip to Downtown Chicago is a breeze. When it comes to planning a show-stopping vacay, you’re the reigning champion of doing it on a dime. You love to plan exciting destination adventures while saving money on a budget.

Hotwire is here to help you plan a smooth sailing trip to Oak Street while saving some major cash. Doubling up on vacation expenses like hotel and car rentals and fun-filled excursions can save you money—especially when you book one of Hotwire’s vacation packages.

If your trip to is spur-of-the-moment and you’re leaving soon, Hotwire can save you up to 60% off your rentals with Hotwire Hot Rate deals. Book with Hotwire to grab a stellar Oak Street flight and hotel package for as low as $630.

Living it up in Downtown Chicago means getting there in style and staying in a hotel that matches your mood. Book one of Hotwire’s Oak Street, Downtown Chicago vacation packages to enjoy the best of both worlds. Flight and hotel packages typically include roundtrip non-stop flights and multi-day hotel stays. Packages are priced per person and are perfect for flying solo or traveling with a group of friends or family. Conveniently choose from Hotwire’s inventory of hotels in Oak Street for some of the best accommodations and flight deals.

FAQs about cheap Oak Street packages:

How to get cheap vacation deals to Oak Street?

Save up to 60% off vacation deals with Hotwire Hot Rates. Just plug in your general preferences and let Hotwire choose matching hotels for as low as $94.

How much are Oak Street packages?

Vacation packages to Oak Street vary in price. They are priced per person and include discounted hotel and flight costs. With Hotwire, you can score a vacation package for as low as $630.

How to find cheap car rentals near Oak Street?

Hotwire partners with some of the most reliable car rental companies in Downtown Chicago to bring you the best car rental deals in Oak Street for as low as . Select a rental from Hotwire’s extensive inventory of cars for every travel style. If you plan on bringing friends or family along, opt for a spacious SUV. If you’re visiting on business but still plan to make time for off-the-clock adventures, Hotwire offers sleek luxury and convertible rentals.

Is it safe to travel to Oak Street now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Oak Street right now?” When it’s time to book your vacation, check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.