--- title: "Grand Boulevard Holidays 2026 from £855 | Expedia.co.uk" description: "Book your ATOL protected Grand Boulevard holiday today! Enjoy flexibility with our interest-free instalments & book now pay later option. Fully refundable rates on most hotels." canonical: "https://www.expedia.co.uk/Grand-Boulevard.d6132310.Holidays-City-Breaks" language: en-GB market: GB currency: GBP prices_as_of: 2026-11-14T06:00:28Z --- # Grand Boulevard Holidays from £855 ![A coastal cityscape with a prominent skyscraper and a peninsula extending into the water.](https://images.trvl-media.com/place/6132310/8ecb6fca-f17c-4f52-840d-365b9e5e94e1.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 £750 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 Grand Boulevard Holiday Your next escape is calling your name with a holiday package to Grand Boulevard. Fun, food and nonstop good times — you're sure to find it in this neighbourhood. Eager to explore the sights during your trip to Grand Boulevard? Be sure to check out nearby attractions like [University of Chicago](https://www.expedia.co.uk/University-Of-Chicago-Hyde-Park.d6064081.Attraction), [Chicago Museum of Science and Industry](https://www.expedia.co.uk/Chicago-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Attraction) and [Guaranteed Rate Field](https://www.expedia.co.uk/Guaranteed-Rate-Field-Armour-Square.d6034756.Attraction). Whatever your ideal Grand Boulevard holiday looks like, you can make it a reality with Expedia. ## The Latest Grand Boulevard Holiday 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 bar area with a long counter, multiple stools, and shelves stocked with bottles.](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/0cad890c.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.](https://images.trvl-media.com/lodging/1000000/10000/4200/4200/a96ed6e3.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **27 Dec - 31 Dec** ### [L7 CHICAGO by LOTTE HOTELS + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-27/2026-12-31/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=4200&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.6/10** \- Exceptional (5,243 reviews) "Good location" Reviewed November 14, 2026 Return • Dublin (DUB) - Chicago (ORD) DUB - ORD • Direct ORD - DUB • Direct [~~£1,032~~](https://www.expedia.co.uk/) **£855** per traveller found 17 hours ago - ![A cityscape with a river, a bridge, and a dining area with tables and chairs.](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A high-rise hotel with a prominent 'TRUMP' sign, reflecting in the water, surrounded by other tall buildings.](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/c35e7743.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **27 Dec - 31 Dec** ### [Trump International Hotel & Tower Chicago + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-27/2026-12-31/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.6/10** \- Exceptional (2,075 reviews) Return • Dublin (DUB) - Chicago (ORD) DUB - ORD • Direct ORD - DUB • Direct [~~£1,543~~](https://www.expedia.co.uk/) **£1,215** per traveller found 17 hours ago - ![A rooftop bar with seating and a view of the city skyline at night.](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A hotel room with a dark wooden desk, a mirror, and a sofa with a floral wall art.](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/588bba8b.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **27 Dec - 31 Dec** ### [The Peninsula Chicago + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-27/2026-12-31/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=581213&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.8/10** \- Exceptional (1,000 reviews) Return • Dublin (DUB) - Chicago (ORD) DUB - ORD • Direct ORD - DUB • Direct [~~£1,858~~](https://www.expedia.co.uk/) **£1,513** per traveller found 17 hours ago - ![A rooftop lounge with outdoor seating and a city skyline view.](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![An indoor cafe with tables and chairs, large windows, and a view of the cityscape.](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/b6033176.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **27 Dec - 31 Dec** ### [Pendry Chicago + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-27/2026-12-31/?FromAirport=DUB&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **9.2/10** \- Wonderful (1,164 reviews) "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back." Reviewed November 8, 2026 Return • Dublin (DUB) - Chicago (ORD) DUB - ORD • Direct ORD - DUB • Direct [~~£1,085~~](https://www.expedia.co.uk/) **£886** per traveller found 17 hours 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) **29 Dec - 2 Jan** ### [Hotel Saint Clair- Magnificent Mile + Flight](https://www.expedia.co.uk/go/package/search/FlightHotel/2026-12-29/2027-01-02/?FromAirport=LON&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=49985&dealMarker=&paandie=true&cabinClass=e) Downtown Chicago 4 nights **8.6/10** \- Excellent (2,412 reviews) "Room w/super small and no little fridge." Reviewed November 13, 2026 Return • London (LON) - Chicago (ORD) LHR - ORD • Direct ORD - LHR • 1 stop [~~£1,470~~](https://www.expedia.co.uk/) **£1,231** per traveller found 9 hours ago ## Where to stay in Grand Boulevard Find the best Grand Boulevard areas for the activities you enjoy most. [Learn more about Grand Boulevard](https://www.expedia.co.uk/Chicago-Grand-Boulevard.dx6132310) - [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.co.uk/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.co.uk/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.co.uk/Hotel-Search?pwaOverlay=map®ionId=800025) ### Magnificent Mile Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes. [See properties](https://www.expedia.co.uk/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.co.uk/Hotel-Search?pwaOverlay=map®ionId=800024) ### The Loop Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean. [See properties](https://www.expedia.co.uk/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.co.uk/Hotel-Search?pwaOverlay=map®ionId=6350695) ### 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. [See properties](https://www.expedia.co.uk/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.co.uk/Hotel-Search?pwaOverlay=map®ionId=6059328) ### Lincoln Park Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6059328) ## Discover the most popular places to visit in Grand Boulevard ### Harold Washington Cultural Center Enjoy an outing to Harold Washington Cultural Center during your stay in Chicago. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=658956806039691264) ### Robert S. Abbott Residence Learn about the local history of Chicago with a stop at Robert S. Abbott Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=658954899460087808) ### Richard Wright Residence You can learn about the history of Chicago with a trip to Richard Wright Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=658954497847627776) ### Dr. Daniel Hale Williams Residence You can learn about the history of Chicago with a trip to Dr. Daniel Hale Williams Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=658956235963011072) ### What to do near Grand Boulevard ![360 CHICAGO Observation Deck (Hancock Center)](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [360 CHICAGO Observation Deck](https://www.expedia.co.uk/things-to-do/a.a170348.activity-details?rid=6132310) £18 per adult 86% of travellers recommend ![Skydeck Chicago at Willis Tower ](https://mediaim.expedia.com/localexpert/52615718/4d3e5a90-2f1c-4547-bafd-5de1e2917339.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Skydeck Chicago at Willis Tower](https://www.expedia.co.uk/things-to-do/a.a52615718.activity-details?rid=6132310) £32 per adult 84% of travellers recommend ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=resizecrop&rw=1005&rh=565) #### [Wendella's 90-min Chicago River Architecture Tour](https://www.expedia.co.uk/things-to-do/a.a766175.activity-details?rid=6132310) £30 per adult 94% of travellers recommend [See all activities near Grand Boulevard](https://www.expedia.co.uk/things-to-do/search?rid=6132310) ## Grand Boulevard Hotel Deals ### [Hilton Vacation Club Hotel Blake Chicago](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Vacation-Club-Hotel-Blake-Chicago.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, 4.3 mi from Grand Boulevard - Star rating: 4/5 - Guest rating: 9.6/10 (Exceptional, 1209 reviews) - Price: £100, includes taxes & fees, 10 Dec - 11 Dec ### [Best Western Grant Park Hotel](https://www.expedia.co.uk/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, 3.9 mi from Grand Boulevard - Star rating: 2.5/5 - Guest rating: 8.2/10 (Very good, 2750 reviews) - Price: £77, includes taxes & fees, 7 Dec - 8 Dec ### [Homewood Suites by Hilton Chicago Downtown South Loop](https://www.expedia.co.uk/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, 3.9 mi from Grand Boulevard - Star rating: 3/5 - Guest rating: 8.8/10 (Excellent, 2534 reviews) - Price: £98, includes taxes & fees, 23 Nov - 24 Nov ### [Hyatt Place Chicago/River North](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Place-ChicagoRiver-North.h5501975.Hotel-Information) ![A hotel sign with "HYATT PLACE" written on it, surrounded by tall buildings and street lamps.](https://images.trvl-media.com/lodging/6000000/5510000/5502000/5501975/cadbfabe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 66 W Illinois St, Chicago, IL, 60654, US - Location: River North, 5.4 mi from Grand Boulevard - Star rating: 3.5/5 - Guest rating: 9.2/10 (Wonderful, 1906 reviews) - Price: £113, includes taxes & fees, 23 Nov - 24 Nov ### [Hilton Garden Inn Chicago Downtown South Loop](https://www.expedia.co.uk/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, 3.9 mi from Grand Boulevard - Star rating: 3/5 - Guest rating: 8.8/10 (Excellent, 2205 reviews) - Price: £87, includes taxes & fees, 23 Nov - 24 Nov - Review: No breakfast provided ### [Sable at Navy Pier Chicago, Curio Collection by Hilton](https://www.expedia.co.uk/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, 5.5 mi from Grand Boulevard - Star rating: 4/5 - Guest rating: 9.4/10 (Exceptional, 2762 reviews) - Price: £131, includes taxes & fees, 14 Dec - 15 Dec ### [Embassy Suites by Hilton Chicago Downtown River North](https://www.expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ![A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 600 N State St, Chicago, IL, 60654, US - Location: River North, 5.5 mi from Grand Boulevard - Star rating: 4/5 - Guest rating: 8.6/10 (Excellent, 5980 reviews) - Price: £106, includes taxes & fees, 23 Nov - 24 Nov - Review: My boyfriend enjoyed the breakfast hotel was very nice and clean as well as the rooms! It was overall an amazing hotel! ### [Hyatt House Chicago/West Loop-Fulton Market](https://www.expedia.co.uk/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: 5.2 mi from Grand Boulevard - Star rating: 3.5/5 - Guest rating: 9/10 (Wonderful, 1310 reviews) - Price: £113, includes taxes & fees, 25 Nov - 26 Nov - 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 Grand Boulevard](https://www.expedia.co.uk/Hotel-Search?startDate=2026-11-28&endDate=2026-11-29®ionId=6132310&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Frequently Asked Questions ### How much does a Grand Boulevard travel package cost? From as little as £855, you can create your own Grand Boulevard package. Simply combine hotels, flights and rental cars and we'll reward you with discounts. ### If I'm not able to travel, can I cancel my Grand Boulevard travel package? Your situation can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Grand Boulevard travel package for free if you've booked in the last 24 hours. For bookings older than that, you can still make the necessary changes, but your car rental company, airline or hotel may impose a charge. Want more information? Check out our [Customer Service Portal](https://www.expedia.co.uk/service/?langid=1033). We'll help make sure your trip goes off without a hitch. ### How do I get a cheap travel package to Grand Boulevard? Think of all the thrilling things you could do in Grand Boulevard with extra cash in your wallet. Watch your savings stack up when you combine your hotel and flights into a Grand Boulevard travel package. You have plenty of choice with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 properties across the globe. Whether you're holidaying with the entire family or embarking on a solo adventure, organising a getaway to Grand Boulevard is better with a package. ### Does Expedia offer Book Now, Pay Later Grand Boulevard holidays? Your bank balance shouldn't get in the way of taking a holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a dream getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Consider one of these flexible payment options: - Pay monthly holidays: Klarna has manageable monthly payment plans that work for all types of budgets, so you can escape on that well-deserved holiday now. - Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna. - Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan with Klarna. ### Where should I stay in Grand Boulevard? A journey to Grand Boulevard isn't over until you've seen Millennium Park and Wrigley Field. Book somewhere within walking distance so you can easily access these impressive tourist attractions. ### What are the top hotels in Grand Boulevard? If it's your first time staying in Grand Boulevard, reserve a room at [Hyatt Regency Chicago](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) or [The Godfrey Hotel Chicago](https://www.expedia.co.uk/Chicago-Hotels-The-Godfrey-Hotel-Chicago.h7063210.Hotel-Information). Both hotels offer friendly service and are top options with lots of travellers. ### How far in advance should I book my Grand Boulevard holiday? While not all airlines advertise tickets early, it's usually possible to look up international fares on Expedia up to a year in advance. This is the time you'll bag some incredible bargains. If you've left everything to the last minute, you might still be in luck. Discounted prices occasionally become available a few weeks before departure. ### What does an Expedia Grand Boulevard travel package include? It depends on what sort of escape you have in the works. Grand Boulevard travel deals can include hotels, flights and car rentals. You can mix and match to find the travel package that suits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts. ### What should I know before booking a Grand Boulevard travel package? You can save a tidy sum by bundling your flights, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next unforgettable adventure is only a few clicks away. ### Can I choose my airline with a Grand Boulevard Expedia travel package? Definitely. Expedia has more than 550 partner airlines to pick from around the globe. With such a huge range of choice, finding the right carrier to whisk you off to Grand Boulevard shouldn't be hard. \* 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/ en-SG: https://www.expedia.com.sg/Grand-Boulevard.d6132310.Destination-Travel-Guides ```