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

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
Save 100% on your flight
Price was $341, price is now $210 per person
$210
per person
Nov 16 - Nov 19
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking and a free area shuttle.

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,089, price is now $613 per person
$613
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Save 100% on your flight
Price was $432, price is now $245 per person
$245
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free full breakfast each morning.

Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $669, price is now $404 per person
$404
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $759, price is now $460 per person
$460
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Top Chicago hotels deals

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $179 total per night
$179 total
per night
Oct 26 - Oct 27
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

Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $238 total per night
$238 total
per night
Oct 25 - Oct 26
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
Free airport shuttle
Pet friendly

Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $208 total per night
$208 total
per night
Oct 2 - Oct 3
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Express check-out, luggage storage, and concierge services are also on offer.
Pool
Pet friendly

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $189 total per night
$189 total
per night
Oct 20 - Oct 21
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

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $214 total per night
$214 total
per night
Sep 28 - Sep 29
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

Freehand Chicago
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $160 total per night
$160 total
per night
Oct 20 - Oct 21
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a coffee shop, and a snack bar/deli are also offered.
Pet friendly
Free WiFi
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.

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.

Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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.
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Top all inclusive vacation packages with airfare
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