Deals on vacations and trips to Hometown
Save when you book Hometown package deals
Hometown flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $831, price is now $437 per person
$437
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,040, price is now $570 per person
$570
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,579, price is now $882 per person
$882
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $945, price is now $529 per person
$529
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $921, price is now $520 per person
$520
per person
Mar 25 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Top Hometown hotels deals
Hilton Chicago
720 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $182 total per night
$182 total
Feb 1 - Feb 2
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Pool
Hot Tub
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $94 total per night
$94 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.
Pool
Pet friendly
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $103 total per night
$103 total
Jan 30 - Jan 31
Total with taxes and fees
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-in, and express check-out are also on offer.
Pet friendly
Free WiFi
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$168 nightly
The price is $192 total per night
$192 total
Jan 23 - Jan 24
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.
Pool
Spa
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $126 total per night
$126 total
Jan 19 - Jan 20
Total with taxes and fees
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
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$182 nightly
The price is $214 total per night
$214 total
Feb 8 - Feb 9
Total with taxes and fees
This smoke-free hotel's 4 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A terrace, a snack bar/deli, and express check-in are also on offer.
Free WiFi
Restaurant
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
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Frequently asked questions
Photos of local treasures
Browse Hometown vacation photos for more inspiration
