--- title: "Oakland Vacation Packages 2026 from $293 | Expedia" description: "Bundle Oakland flight + hotel & save up to 100% off your flight with Expedia. FREE cancellation on select hotels." canonical: "https://www.expedia.com/Oakland.d6132392.Destination-Travel-Guides" language: en-US market: US currency: USD prices_as_of: 2026-11-15T12:39:05Z --- # Oakland Vacations from $293 ![A cityscape with modern skyscrapers, a river, and a bridge.](https://images.trvl-media.com/place/6132392/a1e6d62a-9887-4ca4-864e-89c4f18d97fc.jpg?impolicy=fcrop&w=1200&h=300&q=medium) ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $2,000 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your Oakland Vacation With a tailor-made vacation package to Oakland, you'll spend less time planning and more time simply enjoying this appealing neighborhood. From its nature to its walking, there's plenty to discover here. Kick start your trip to Oakland by heading to nearby attractions such as [University of Chicago](https://www.expedia.com/University-Of-Chicago-Hyde-Park.d6064081.Vacation-Attraction), [Chicago Museum of Science and Industry](https://www.expedia.com/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction) and [Guaranteed Rate Field](https://www.expedia.com/Guaranteed-Rate-Field-Armour-Square.d6034756.Vacation-Attraction). No matter your travel goals or budget, booking your ideal Oakland vacation is easy with Expedia. ## The Latest Oakland Vacation Packages Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A modern living room with a sofa, armchairs, and a coffee table. There are bookshelves and a decorative wall panel.](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/7b445c7a.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A tall, modern building with a glass facade and the name "Essen Sex Inn" on the top.](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/d9eeaac7.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 15 - Jan 18** ### [Le Méridien Essex Chicago + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-15/2027-01-18/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=35130365&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 3 nights **9.0/10** \- Wonderful (1,003 reviews) "Wonderful staff!! Welcoming, friendly, and very helpful. We ended up arriving 2 hours before check-in, but staff had no problem helping us out and letting us get our room early. Valet staff hepful when we needed to get an item from the car, James was so awesome helping with luggage and to our room. Housekeeping checked in to see if we were happy with the room, which was very clean!! Each contact we had with staff was a positive one. Lobby was small but cute and eclectic. Wish there was a..." Reviewed November 14, 2026 Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$418~~](https://www.expedia.com/) **$293** per traveler found 1 day ago - ![An outdoor seating area with a glass table, orange cushions, and potted plants.](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4a14c915.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern hotel lobby with a bar area, seating arrangements, and decorative lighting.](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4c0ebbe4.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Dec 21 - Dec 25** ### [Sheraton Grand Chicago Riverwalk + Flight](https://www.expedia.com/go/package/search/FlightHotel/2026-12-21/2026-12-25/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12167&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **8.6/10** \- Excellent (1,890 reviews) Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop MDW - ATL • Nonstop [~~$843~~](https://www.expedia.com/) **$572** per traveler found 1 day ago - ![A modern restaurant interior with a bar area, seating, and a wooden table.](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/2489547a.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern interior with a dining area, sofas, and artwork on the walls.](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/a69b3429.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 15 - Jan 18** ### [Hotel Saint Clair- Magnificent Mile + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-15/2027-01-18/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=49985&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 3 nights **8.6/10** \- Excellent (2,421 reviews) "Loved staying here! Beautiful property! Lovely room and amenities! Can’t wait to start again!!" Reviewed November 15, 2026 Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$449~~](https://www.expedia.com/) **$309** per traveler found 1 day ago - ![A high-rise building with a modern architectural design, featuring a grid-like facade and large windows.](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/f2c6847b.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A bar area with a marble countertop, bar stools, and a variety of bottles.](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/w2990h1178x0y0-a3dcd2ef.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 28 - Jan 31** ### [Hotel Riu Plaza Chicago + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-28/2027-01-31/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=102622712&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 3 nights **9.4/10** \- Exceptional (5,713 reviews) Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$502~~](https://www.expedia.com/) **$348** per traveler found 1 day ago - ![A modern living room with a large window overlooking a body of water, a tripod, and a sofa.](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Jan 28 - Jan 31** ### [Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight](https://www.expedia.com/go/package/search/FlightHotel/2027-01-28/2027-01-31/?FromAirport=ATL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=57651125&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 3 nights **9.4/10** \- Exceptional (2,765 reviews) Roundtrip • Atlanta (ATL) - Chicago (ORD) ATL - ORD • Nonstop ORD - ATL • Nonstop [~~$886~~](https://www.expedia.com/) **$629** per traveler found 1 day ago ## Where to stay in Oakland Find the best Oakland areas and neighborhoods for the activities you enjoy most. [Learn more about Oakland](https://www.expedia.com/Chicago-Oakland.dx6132392) - [Downtown Chicago](#) - [Magnificent Mile](#) - [The Loop](#) - [River North](#) - [Lincoln Park](#) ![A cityscape with tall skyscrapers and a historic tower.](https://images.trvl-media.com/place/6350699/b1dbe458-cfee-4a77-aafa-ed727f3811c2.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Downtown Chicago](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=6350699) ### Downtown Chicago The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. [See properties](https://www.expedia.com/Hotel-Search?regionId=6350699) ![A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.](https://images.trvl-media.com/place/800025/6670c4dd-6c2f-482d-8f82-0db84866cc03.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) Photo by © City of Chicago [View properties in map for Magnificent Mile](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=800025) ### Magnificent Mile Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. [See properties](https://www.expedia.com/Hotel-Search?regionId=800025) ![A river with yellow boats, a bridge, and tall buildings.](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for The Loop](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=800024) ### The Loop Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. [See properties](https://www.expedia.com/Hotel-Search?regionId=800024) ![A large, historic building with a central tower and multiple windows, located near a body of water.](https://images.trvl-media.com/place/6069193/0e27114d-eb41-46f9-b005-6ab55df346d2.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for River North](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=6350695) ### River North Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. [See properties](https://www.expedia.com/Hotel-Search?regionId=6350695) ![A river with a city skyline in the background, surrounded by green trees and grass.](https://images.trvl-media.com/place/507390/bb079d23-ceff-41ef-802e-0533da68eac7.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [View properties in map for Lincoln Park](https://www.expedia.com/Hotel-Search?pwaOverlay=map®ionId=6059328) ### Lincoln Park Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads. [See properties](https://www.expedia.com/Hotel-Search?regionId=6059328) ## Discover the most popular places to visit in Oakland ### 41st Street Beach Why not spend a lazy afternoon at 41st Street Beach during your trip to Chicago? Stroll along the beaches or visit the shops while you're in the area. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248635983988998) ## Oakland Hotel Deals ### [Best Western Grant Park Hotel](https://www.expedia.com/Chicago-Hotels-Best-Western-Grant-Park-Hotel.h23023.Hotel-Information) ![A restaurant interior with round tables and chairs, a bamboo-themed wall mural, and wall-mounted lighting fixtures.](https://images.trvl-media.com/lodging/1000000/30000/23100/23023/11c047f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1100 S Michigan Ave, Chicago, IL, 60605, US - Location: The Loop, 3.3 mi from Oakland - Star rating: 2.5/5 - Guest rating: 8.2/10 (Very good, 2754 reviews) - Price: $86 nightly, $102 total, Dec 7 - Dec 8, Total with taxes and fees ### [Sable at Navy Pier Chicago, Curio Collection by Hilton](https://www.expedia.com/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![A modern living room with a large window overlooking a body of water, a tripod, and a sofa.](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 900 E Grand, Chicago, IL, 60611, US - Location: Streeterville, 4.7 mi from Oakland - Star rating: 4/5 - Guest rating: 9.4/10 (Exceptional, 2765 reviews) - Price: $140 nightly, $167 total, Dec 15 - Dec 16, Total with taxes and fees ### [Hilton Vacation Club Hotel Blake Chicago](https://www.expedia.com/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) ![A hotel entrance with a marquee sign, a blue carpet, and a flag.](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/e4432fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 500 South Dearborn Street, Chicago, IL, 60605, US - Location: The Loop, 3.8 mi from Oakland - Star rating: 4/5 - Guest rating: 9.6/10 (Exceptional, 1210 reviews) - Price: $111 nightly, $132 total, Dec 10 - Dec 11, Total with taxes and fees ### [Le Méridien Essex Chicago](https://www.expedia.com/Chicago-Hotels-Hotel-Essex-Chicago.h35130365.Hotel-Information) ![A modern living room with a sofa, armchairs, and a coffee table. There are bookshelves and a decorative wall panel.](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/7b445c7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 800 S Michigan Ave, Chicago, IL, 60605, US - Location: The Loop, 3.5 mi from Oakland - Star rating: 4/5 - Guest rating: 9/10 (Wonderful, 1003 reviews) - Price: $127 nightly, $151 total, Dec 7 - Dec 8, Total with taxes and fees - Review: "Wonderful staff!! Welcoming, friendly, and very helpful. We ended up arriving 2 hours before check-in, but staff had no problem helping us out and letting us get our room early. Valet staff hepful when we needed to get an item from the car, James was so awesome helping with luggage and to our room. Housekeeping checked in to see if we were happy with the room, which was very clean!! Each contact we had with staff was a positive one. Lobby was small but cute and eclectic. Wish there was a... ### [Hilton Garden Inn Chicago Downtown South Loop](https://www.expedia.com/Chicago-Hotels-Hilton-Garden-Inn-Chicago-Downtown-South-Loop.h33682469.Hotel-Information) ![A hot tub with a metal ladder, surrounded by white tiled walls and floor, with a large window providing a view of the cityscape.](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/5bee96cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 55 E 11th Street, Chicago, IL, 60605, US - Location: The Loop, 3.4 mi from Oakland - Star rating: 3/5 - Guest rating: 8.8/10 (Excellent, 2207 reviews) - Price: $97 nightly, $114 total, Nov 23 - Nov 24, Total with taxes and fees ### [Homewood Suites by Hilton Chicago Downtown South Loop](https://www.expedia.com/Chicago-Hotels-Homewood-Suites-By-Hilton-Chicago-Downtown-South-Loop.h33387384.Hotel-Information) ![A modern kitchen with a large window, a dining area, and a view of the sea.](https://images.trvl-media.com/lodging/34000000/33390000/33387400/33387384/d2ddfcbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 59 E. 11th Street, Chicago, IL, 60605, US - Location: The Loop, 3.3 mi from Oakland - Star rating: 3/5 - Guest rating: 8.8/10 (Excellent, 2537 reviews) - Price: $106 nightly, $126 total, Nov 23 - Nov 24, Total with taxes and fees ### [ACME Hotel Chicago, Outset Collection by Hilton](https://www.expedia.com/Chicago-Hotels-ACME-Hotel-Company.h886306.Hotel-Information) ![A bar area with a checkered floor, bar stools, and a well-lit sign above the bar.](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/w5790h3840x5y0-6230cc3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 15 East Ohio Street, Chicago, IL, 60611, US - Location: River North, 4.9 mi from Oakland - Star rating: 3.5/5 - Guest rating: 9/10 (Wonderful, 1930 reviews) - Price: $85 nightly, $101 total, Dec 7 - Dec 8, Total with taxes and fees ### [Hyatt House Chicago/West Loop-Fulton Market](https://www.expedia.com/Chicago-Hotels-Hyatt-House-Chicago-West-Loop.h35834237.Hotel-Information) ![A modern lounge area with seating, a bar, and large windows offering views.](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/db5b7e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 105 N MAY STREET, Chicago, IL, 60607, US - Location: 4.9 mi from Oakland - Star rating: 3.5/5 - Guest rating: 9/10 (Wonderful, 1310 reviews) - Price: $139 nightly, $166 total, Nov 25 - Nov 26, Total with taxes and fees - Review: Clean spacious room for a great price 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. [See all properties in Oakland](https://www.expedia.com/Hotel-Search?startDate=2026-11-29&endDate=2026-11-30®ionId=6132392&adults=2&sort=RECOMMENDED&openPlayBack=true) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/ es-MX: https://www.expedia.mx/Oakland.d6132392.Guia-de-vacaciones ```