Title: Crestwood Vacation Packages 2026 from $640 | Expedia.com [Crestwood Travel Guide](https://expedia.com/Crestwood.dx6960)[Hotels in Crestwood](https://expedia.com/Crestwood-Hotels.d6960.Travel-Guide-Hotels)[Vacation Rentals in Crestwood](https://expedia.com/Crestwood-Vacation-Rentals.d6960.Travel-Guide-VacationRentals)[Flights to Crestwood](https://expedia.com/Cheap-Flights-To-Crestwood.d6960.Travel-Guide-Flights)[Things to do in Crestwood](https://expedia.com/Things-To-Do-In-Crestwood.d6960.Travel-Guide-Activities)[Car Rentals in Crestwood](https://expedia.com/Car-Rentals-In-Crestwood.d6960.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6960/240c7639-252c-425c-9300-8c5e47f6e396.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Crestwood Vacations from $640 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 Crestwood Vacation With plenty of highlights as well as hidden gems, this city is best explored with a Crestwood vacation package. Book a hotel in Hyde Park, which is good for history, nature and culture. A trip to Crestwood is a superb opportunity to do some sightseeing. Be sure to stop by well-known attractions like [Chicago Ridge Shopping Mall](https://www.expedia.com/Chicago-Ridge-Shopping-Mall-Chicago.d6143658.Vacation-Attraction), [Trinity Christian College](https://www.expedia.com/Trinity-Christian-College-Chicago.d6143660.Vacation-Attraction) and [Orland Square](https://www.expedia.com/Orland-Square-Chicago.d553248635976375725.Vacation-Attraction). Whatever your travel plans or budget, organizing your ultimate tailored Crestwood vacation is a piece of cake with Expedia. ## The Latest Crestwood vacation packages Price found within the past 48 hours. Click for updated prices. ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago $640 per person Jun 4 - Jun 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.6/10 Excellent! (2,076 reviews) Staff was soooo friendly Reviewed on Mar 25, 2026 ![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 Save 100% on your flight $830 per person Jun 4 - Jun 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Would be nice if I had better view Reviewed on Mar 25, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago Save 100% on your flight $704 per person Jun 18 - Jun 21 found 24 hours ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9/10 Wonderful! (441 reviews) Staff was really nice Reviewed on Mar 24, 2026 ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago Save 100% on your flight $685 per person Jun 4 - Jun 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent. Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value Reviewed on Mar 24, 2026 ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Chicago - Magnificent Mile Downtown Chicago Save 100% on your flight $1,125 per person Jun 6 - Jun 12 found 8 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.8/10 Excellent! (2,357 reviews) Convenient location and clean hotel... Reviewed on Mar 24, 2026 Don't see what you're looking for? See all available trips from Columbus to Crestwood [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-26/2026-05-03/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Crestwood ![Wrigley Field featuring cbd, a sporting event and a city](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.com/Wrigley-Field-Lakeview.d6034754.Vacation-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 enjoy some retail therapy 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.com/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Chicago Skyline at North Beach](https://images.trvl-media.com/place/6069213/e3e08680-ba57-4e08-8e19-fef490757e5e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naval Base Great Lakes After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area. [](https://expedia.com/Naval-Base-Great-Lakes-Chicago.d6069213.Vacation-Attraction) ### What to do in Crestwood ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck $27 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Chicago Bulls Basketball Game at United Center](https://mediaim.expedia.com/localexpert/47300776/972792e4-c31c-4347-9c2d-8d50ffbad913.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Bulls Basketball Game at United Center $66 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/chicago-bulls-basketball-game-at-united-center.a47300776.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 $41 per adult **94%** of travellers recommend [](https://expedia.com/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) [See all activities in Crestwood](https://expedia.com/things-to-do/search?rid=6960) ## Crestwood Hotel Deals ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL Fully refundableReserve now, pay when you stay $110 nightly $129 total Apr 1 - Apr 2 Total with taxes and fees 8/10 Very Good! (10,023 reviews) The rooms are very outdated and the bathroom was a mess when I arrived. (Like hair in the shower) The hotel is very conveniently located so that is a huge plus and not super expensive. I felt safe the whole time, and staff was helpful when I arrived. Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6960) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL Fully refundableReserve now, pay when you stay $122 nightly $143 total Apr 6 - Apr 7 Total with taxes and fees 9/10 Wonderful! (3,980 reviews) This place is amazing, great amenities and staff, coffee bar is great, bartender girl NOT very nice of friendly, I would stay again, stores and museums very near by, room was super clean and comfortable definitely recommend it and I would stay there again. Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6960) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_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 $130 nightly $153 total Apr 5 - Apr 6 Total with taxes and fees 8.6/10 Excellent! (5,774 reviews) The pillows in the rooms were very hard and so was the bed. In the pool area there where not enough towels for people and it seemed very cold for a indoor pool. Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6960) [See all 3,677 properties in Crestwood](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F27%2F2026&endDate=3%2F28%2F2026®ionId=6960) 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. ## Find the Best Crestwood Vacation Packages ## Crestwood Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | | Population | 11,000 | | Max Temp Winter | 30ºF | | Max Temp Summer | 80ºF | | Top Sights | [Calumet Beach](https://www.expedia.com/Calumet-Beach-Chicago.d553248635983994343.Vacation-Attraction), [Galloping Ghost](https://www.expedia.com/Galloping-Ghost-Chicago.d553248621532658619.Vacation-Attraction) and [Midwest Carvers Museum](https://www.expedia.com/Midwest-Carvers-Museum-Chicago.d6187180.Vacation-Attraction) | ## More vacations you might like ![](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 Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.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 Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.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 Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.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 Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.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 Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations 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.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Crestwood vacation package cost? ### What are the cheapest months to go to Crestwood? ### How many days is enough for Crestwood? ### How to find the best Crestwood package deals? ### Is it cheaper to book a Crestwood vacation as a package? ### When to book a vacation package to Crestwood? ### How to plan a trip to Crestwood? > 1. Pick your dates: What you'd like to do in Crestwood and your preferred season will help you decide when to travel. > 2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will likely be the largest expense during your trip to Crestwood. > 3. Organize your Crestwood getaway with our [trip planning tool](https://www.expedia.com/why/trip-planning): Look for and book hotels and experiences all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Crestwood together. > 4. Decide how many days away: Start by making a list of all the activities and attractions you'd like to experience in Crestwood. Then, estimate how long you'll need for each, as well as any travel time. > 5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to find a Crestwood vacation package that brings all your bookings together. > 6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some exciting [things to do in Crestwood](https://www.expedia.com/Things-To-Do-In-Crestwood.d6960.Travel-Guide-Activities) in Crestwood. Book tickets or make reservations before you go to save time and avoid the hassle of looking for activities once you arrive. ### Does Expedia offer Book Now, Pay Later Crestwood vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Alsip Hotels ](https://www.expedia.com/Alsip-Hotels.d6302.Travel-Guide-Hotels) - [Cheap Hotels in Alsip ](https://www.expedia.com/Alsip-Hotels-Cheap-Hotels.0-0-d6302-tCheapHotels.Travel-Guide-Filter-Hotels) - [Motels in Alsip ](https://www.expedia.com/Alsip-Motels.d6302-aaMotels.Travel-Guide-Accommodation) - [Hotels with a Pool in Alsip ](https://www.expedia.com/Alsip-Hotels-Hotel-With-Pool.0-0-d6302-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Alsip ](https://www.expedia.com/Alsip-Hotels-Hotels-With-Indoor-Pool.0-0-d6302-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - 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