
Deals on vacations and trips to Chicago
Save when you book Chicago package deals
Chicago flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Holiday Inn Chicago O'Hare Area by IHG
O'Hare
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Free self parking, a coffee shop, and a snack bar/deli are also offered.

Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A nightclub, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the a rooftop terrace, bar/lounge, and coffee shop.

Art Villa
West Town
Save 100% on your flight
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.

Illinois Beach Hotel
Save 100% on your flight
per person
Aug 12 - Aug 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.
Top Chicago hotels deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Free Cancellation
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.
Pool
Spa

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.
Pool
Breakfast included

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.
Free WiFi
Restaurant

The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.
Breakfast included
Pet friendly
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.
Popular places to visit

Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Michigan Avenue
4.5/5(332 reviews)
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.
Frequently asked questions
Where to stay in Chicago: Best areas for travelers
- Downtown Chicago: Full of atmosphere and ambiance, this is a perfect match if you love being in the thick of the action. Choose a comfortable room at the theWit Chicago - a DoubleTree by Hilton Hotel, the Renaissance Chicago Downtown Hotel or the Cambria Hotel Chicago Loop - Theatre District. Then, you'll be ideally placed to discover this neighborhood's best attractions, like Navy Pier and Chicago Children's Museum.
- Near North Side: You've got lots of options when it comes to welcoming places to stay in this neighborhood. To start with, look up the Waldorf Astoria Chicago, The Talbott Hotel and the FieldHouse Jones. You'll be able to jump out of bed and be at terrific attractions like Navy Pier soon after.
- Lakeview: If the reason for your travels is to check off the major attractions, staying here is a wise choice. Make yourself comfortable at The Wheelhouse Hotel, the City Suites Hotel or the Best Western Plus Hawthorne Terrace Hotel. Of the area's many highlights, the crowd favorite is Wrigley Field.
- West Town: If you're on the hunt for someplace to stay in this area, the Ruby Room , the Beautiful Modern Bright And Open West Town Single Family Home and The Robey are convenient options. Creative types in particular will enjoy this part of town, with Ukrainian Institute Of Modern Art and Chicago Center for the Performing Arts among the many sights available here.
- The Loop: If you only have time to discover one attraction in this neighborhood, make a beeline for Millennium Park. Take in this well-known sight at your own pace and then head on back to the Palmer House a Hilton Hotel. The Congress Plaza Hotel and the Chicago Athletic Association also have everything you need for a pleasant stay.
Photos of local treasures
Browse Chicago vacation photos for more inspiration





Top all inclusive vacation packages with airfare
Book a vacation to Chicago
Most popular
Hotels
Cheap Hotels in GurneeCheap Hotels in EvanstonDowntown Chicago Hotels with Free ParkingCheap Hotels in Oak BrookDowntown Chicago Hotels with Hot TubsCheap Hotels in SkokieHotels around Michigan AvenueHotels around Millennium ParkCheap Hotels in LombardCheap Hotels in WaukeganHotels around Grant ParkCheap Hotels in BolingbrookHotels around Allstate ArenaCheap Hotels in SchaumburgCheap Hotels in RosemontCheap Hotels in NorthbrookHotels around Navy PierHotels around Naval Base Great LakesCheap Hotels in NapervilleHotels in Downtown ChicagoHotels around Soldier FieldHotels around Rivers Casino
Cars
Activities