Chicago Holidays from £743
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to £335 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
Top Chicago Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,501, price is now £979 per person
£979
per person
24 Oct - 28 Oct
found 6 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
You were being taken care of felt like home away from home good job to the staff at the Trump tower Chicago
Reviewed on 12 Sept 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was £1,160, price is now £769 per person
£769
per person
24 Oct - 28 Oct
found 6 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
The rooms were not very well decorated. The furniture used in the room looks like furniture from a detention house. Not my favorite.
Reviewed on 8 Sept 2025
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Price was £1,226, price is now £836 per person
£836
per person
23 Oct - 30 Oct
found 9 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (237 reviews)
Clean hotel near the United Center. Many fast food options nearby.
Reviewed on 13 Sept 2025
Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Chicago Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 2,720,500 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Chicago Riverwalk, Shedd Aquarium and Art Institute of Chicago |
Top hotels in Chicago
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £150 per night from 22 Sept to 23 Sept
£150
22 Sept - 23 Sept
includes taxes & fees
8.4/10 Very Good! (4,894 reviews)
"From the moment we walked in, early for our reservation, we were treated like the number one priority by every staff member. The bellman #johnnyBravo #JimmyNeutron #JohnnyDanger thank you for your comic relief after a long morning of travel and for keeping our belongings safe! The room was very clean ..."
Reviewed on 10 Sep 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £128 per night from 22 Sept to 23 Sept
£128
22 Sept - 23 Sept
includes taxes & fees
7.8/10 Good! (9,162 reviews)
"The rooms need to be refurbished.,,,bathroom not as clean as I would expect. But the hotel is over 100 yrs old."
Reviewed on 10 Sep 2025
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £156 per night from 22 Sept to 23 Sept
£156
22 Sept - 23 Sept
includes taxes & fees
8.4/10 Very Good! (3,863 reviews)
"The staff was friendly and helpful."
Reviewed on 10 Sep 2025
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 find the perfect gifts to bring home 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.
What to do in Chicago
Wendella's 90-min Chicago River Architecture Tour
£33
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
£33
per adult
96% of travellers recommend
More trip options
Expedia's Latest Trends
Hotels
Flights
Activities
Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
