Title: Oakland Holidays 2026 from £670 | Expedia.co.uk [Hotels in Oakland](https://expedia.co.uk/Oakland-Chicago-Hotels.0-n6132392-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Oakland Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Oakland.d6132392.Car-Hire-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Oakland Holidays from £670 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ### Your Oakland Holiday Book a customized holiday package to Oakland and experience the wonders of this neighbourhood from morning till night. From its nature and walking to its unique vibe and personality, there are plenty of fantastic reasons to visit Oakland. Not sure what to see and do during your trip to Oakland? Nearby attractions like [University of Chicago](https://www.expedia.co.uk/University-Of-Chicago-Hyde-Park.d6064081.Attraction), [Soldier Field](https://www.expedia.co.uk/Soldier-Field-South-Loop.d6058043.Attraction) and [John G. Shedd Aquarium](https://www.expedia.co.uk/John-G-Shedd-Aquarium-Chicago.d6065141.Attraction) are great places to start. No matter what your ideal Oakland holiday looks like, you can make it a reality with Expedia. Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago £670 per person 5 May - 8 May found 1 day ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean amenities, amazing food, and great service! Reviewed on 27 Feb 2026 ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wade Downtown Chicago £1,287 per person 9 May - 16 May found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 8.4/10 Very Good! (1,444 reviews) Room was very clean would return again Reviewed on 23 Feb 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £1,054 per person 5 May - 8 May found 1 day ago Return direct flight included London (LGW) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) We had a great stay! Reviewed on 23 Feb 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago £688 per person 2 Apr - 6 Apr found 1 hour ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Room smelled like food but overall very clean, very great service and staff both night and morning shift. Reviewed on 16 Feb 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago £765 per person 2 Apr - 6 Apr found 1 day ago Return direct flight included Dublin (DUB) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Had a great stay!! Kelly at the front desk was so sweet Reviewed on 22 Feb 2026 ## Where to stay in Oakland Find the best Oakland areas and neighborhoods for the activities you enjoy most. [Learn more about Oakland](https://expedia.co.uk/Chicago-Oakland.dx6132392) ![Downtown Chicago featuring a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Chicago 4 out of top 10 points of interest in this area The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. [Find hotels in Downtown Chicago](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6350699) ![Magnificent Mile - River North](https://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Magnificent Mile Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes. [Find hotels in Magnificent Mile](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=800025) ![The Loop - Downtown featuring a river or creek](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(187 area reviews) Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean. [Find hotels in The Loop](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=800024) ![River North showing railway items, street scenes and a city](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### River North Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city. [Find hotels in River North](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6350695) ![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### O'Hare 3.5/5(10 area reviews) Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago. [Find hotels in O'Hare](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635074842747) ## Top hotels in Oakland ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL Fully refundableReserve now, pay when you stay £77 28 Feb - 1 Mar includes taxes & fees 8/10 Very Good! (9,892 reviews) We mainly go to Chicago for medical appointments and it is \*so awesome\* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ... Reviewed on 27 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6132392) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Riu Plaza Chicago 150 East Ontario Street Chicago IL Fully refundableReserve now, pay when you stay £119 4 Mar - 5 Mar includes taxes & fees 9.4/10 Exceptional! (3,421 reviews) Great service Reviewed on 27 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=6132392) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL Fully refundableReserve now, pay when you stay £98 2 Mar - 3 Mar includes taxes & fees 8.6/10 Excellent! (5,691 reviews) Was suppose to get connecting rooms and did not, In both rooms both remotes and phones did not work, we stood 2 nights and no one cleaned our room, not enough towels. The garage was great ! Valet was on point every time ! Reviewed on 27 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=02%2F03%2F2026&endDate=03%2F03%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132392) [See all 4,698 properties in Oakland](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F02%2F2026&endDate=01%2F03%2F2026®ionId=6132392) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## Frequently asked questions ### How much does an Oakland travel package cost? ### If I'm not able to travel, can I cancel my Oakland travel package? ### How do I get a cheap travel package to Oakland? ### Does Expedia offer Book Now, Pay Later Oakland holidays? > - Pay monthly holidays: Klarna offers convenient monthly payment plans that fit all budgets, so you can jet away on that well-earned holiday sooner. > - Pay in instalments holidays: If you'd like to pay off your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna. > - Low deposit holidays: Clicking on the "book now" button is easier with this payment plan. Just put down a small deposit on your booking and then get on your way. ### Where should I stay in Oakland? ### What are the top hotels in Oakland? ### How far in advance should I book my Oakland holiday? ### What does an Expedia Oakland travel package include? ### What should I know before booking an Oakland travel package? ### Can I choose my airline with an Oakland Expedia travel package? ### Popular places to visit ![Wrigley Field featuring a city, a sporting event and city views](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction) ![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.co.uk/Michigan-Avenue-Downtown-Chicago.d6156167.Attraction) ![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.co.uk/Navy-Pier-Downtown-Chicago.d6069215.Attraction) ### Things to do ![Skydeck - Willis Tower Admission ](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skydeck - Willis Tower Admission £32 per adult **98%** of travellers recommend [](https://expedia.co.uk/things-to-do/skydeck-willis-tower-admission.a1342523.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago £28 per adult **98%** of travellers recommend [](https://expedia.co.uk/things-to-do/flyover-in-chicago.a50023979.activity-details) ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour £30 per adult **94%** of travellers recommend [](https://expedia.co.uk/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) [See all activities in Chicago](https://expedia.co.uk/things-to-do/search?rid=6132392) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.