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Holidays to Chicago

Choose two or more items and save on your trip:

Plan your Chicago holiday with Expedia

  • Our 2020 bundled deals are currently unavailable, but you can now book our 2021 holiday packages deals. Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Chicago. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation* , because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page. 
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

2021 Chicago holiday deals

FairBridge Inn Express Melrose Park

FairBridge Inn Express Melrose Park

3.5 out of 5

£466

per person
15 Mar - 19 Mar
Return flight included
London (LON) to Chicago (ORD)
2.3/5 (726 reviews)

"It is in an acceptable area, only at night they make a lot of noise, the sheets do not look clean and it smells musty.…"

Reviewed on 2 Aug 2020

The Langham, Chicago

The Langham, Chicago

5 out of 5
River North

£849

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.9/5Exceptional! (1,209 reviews)

"This was one of the best stays I’ve ever had! From the staff, to the cleanliness of the rooms, to the attention! Everything was beyond amazing, thank you Langham for setting the bar and keeping it there, even through a pandemic. I can’t wait to be back!…"

Reviewed on 20 Oct 2020

Conrad Chicago

Conrad Chicago

4.5 out of 5
River North

£832

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.7/5Exceptional! (756 reviews)

"Decor is somewhat dated, but otherwise a nice place.…"

Reviewed on 8 Mar 2020

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Streeterville

£1,135

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.9/5Exceptional! (999 reviews)

"This was one of the best check ins I’ve ever experienced. The staff was exceptionally nice and very helpful, especially the valet team. This hotel is so beautiful and it makes you not want to leave. This was an unforgettable experience. Thank ALL staff for the wonderful stay.…"

Reviewed on 18 Oct 2020

LEVEL Chicago – Old Town

LEVEL Chicago – Old Town

4 out of 5
River North

£943

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.5/5Wonderful! (43 reviews)

"I loveeeee LEVEL Chicago.Very modern and clean. Will be visiting again this week!…"

Reviewed on 7 Jun 2020

Kasa Chicago River North Apartments

Kasa Chicago River North Apartments

4 out of 5
River North

£685

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.4/5Excellent! (7 reviews)

"Great experience at Kasa Chicago River North. Smooth check in and any questions asked during the trip was resolved quickly. I would highly recommend staying at this location!…"

Reviewed on 25 Sep 2020

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Top flight + hotel deals in Chicago

The Langham, Chicago

The Langham, Chicago

5 out of 5
River North

£849

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.9/5Exceptional! (1,209 reviews)

"This was one of the best stays I’ve ever had! From the staff, to the cleanliness of the rooms, to the attention! Everything was beyond amazing, thank you Langham for setting the bar and keeping it there, even through a pandemic. I can’t wait to be back!…"

Reviewed on 20 Oct 2020

Conrad Chicago

Conrad Chicago

4.5 out of 5
River North

£832

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.7/5Exceptional! (756 reviews)

"Decor is somewhat dated, but otherwise a nice place.…"

Reviewed on 8 Mar 2020

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Streeterville

£1,135

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.9/5Exceptional! (999 reviews)

"This was one of the best check ins I’ve ever experienced. The staff was exceptionally nice and very helpful, especially the valet team. This hotel is so beautiful and it makes you not want to leave. This was an unforgettable experience. Thank ALL staff for the wonderful stay.…"

Reviewed on 18 Oct 2020

LEVEL Chicago – Old Town

LEVEL Chicago – Old Town

4 out of 5
River North

£943

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.5/5Wonderful! (43 reviews)

"I loveeeee LEVEL Chicago.Very modern and clean. Will be visiting again this week!…"

Reviewed on 7 Jun 2020

Kasa Chicago River North Apartments

Kasa Chicago River North Apartments

4 out of 5
River North

£685

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.4/5Excellent! (7 reviews)

"Great experience at Kasa Chicago River North. Smooth check in and any questions asked during the trip was resolved quickly. I would highly recommend staying at this location!…"

Reviewed on 25 Sep 2020

Residence Inn Chicago Downtown/Loop

Residence Inn Chicago Downtown/Loop

3.5 out of 5
The Loop

£681

per person
8 Jan - 13 Jan
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
4.7/5Exceptional! (923 reviews)

"This had to one of my best stays ever! The staff was nice and helpful and my suite was very clean. I also liked how there were tissue boxes near every elevator so that I did not have to touch the buttons.…"

Reviewed on 12 Oct 2020

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Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
    Downtown Chicago featuring a city

    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.

    Find hotels in Downtown Chicago
    Magnificent Mile - River North

    Magnificent Mile

    Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

    Find hotels in Magnificent Mile
    The Loop - Downtown featuring a river or creek

    The Loop

    3 out of top 10 points of interest in this area

    4.5/5Wonderful!(187 area reviews)

    Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

    Find hotels in The Loop
    Shops at North Bridge featuring street scenes, cbd and a city

    River North

    Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like House of Blues Chicago and Chicago Riverwalk are major draws. Catch the metro at Chicago Station (Brown Line) or Merchandise Mart Station to see more of the city.

    Find hotels in River North
    Robie House

    Hyde Park

    3/5(1 area review)

    Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Chicago Museum of Science and Industry and Robie House.

    Find hotels in Hyde Park

Top Hotel Deals

LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by Hilton
4.5 out of 5
85 East Wacker Drive, Chicago, IL
The price is £103 per night from 11 Nov to 12 Nov

Located in The Loop, this luxury hotel is steps away from Chicago Riverwalk and Michigan Avenue. Grant Park and Chicago Theatre are also within 10 minutes. Clark-Lake ...…

4.6/5Wonderful! (2,494 reviews)

"Had a great time! Loved the location. Staff was amazing and the rooftop bar was BEAUTIFUL!"…"

Reviewed on 20 Oct 2020

LondonHouse Chicago, Curio Collection by Hilton
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
4.5 out of 5
20 E Chestnut St, Chicago, IL
The price is £139 per night from 23 Nov to 24 Nov

Located in Near North Side, this luxury hotel is within a 5-minute walk of State Street, Water Tower Place, and John Hancock Center. Chicago Water Tower and ...…

4.6/5Wonderful! (1,793 reviews)

"Checking in was a breeze. Hotel was really clean and the bed was amazing!"…"

Reviewed on 19 Oct 2020

Sofitel Chicago Magnificent Mile
Best Western Grant Park Hotel
Best Western Grant Park Hotel
2.5 out of 5
1100 S Michigan Ave, Chicago, IL
The price is £51 per night from 26 Oct to 27 Oct

Located in The Loop, this hotel is within a 10-minute walk of Grant Park and Columbia College Chicago. Field Museum of Natural History and John G. Shedd Aquarium ...…

4/5Very Good! (3,018 reviews)

"Location is good Nothing especial No breakfast No lobby room"…"

Reviewed on 21 Oct 2020

Best Western Grant Park Hotel
See all 2318 properties in Chicago
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.

Top things to do in Chicago

360 CHICAGO Observation Deck (Hancock Center)
Image for 360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck (Hancock Center)

£19
Per adult
84% of travellers recommend
Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions
Image for Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions

Go Chicago Explorer Pass: Choose 3, 4 or 5 Top Attractions

£64
Per adult
80% of travellers recommend
The Field Museum
Image for The Field Museum

The Field Museum

£20
Per adult
92% of travellers recommend
See all activities in Chicago

Frequently asked questions

Does Expedia have holiday package deals to Chicago?
Get instant savings by booking a Chicago holiday package. Just pick your favourite options and let Expedia take care of the rest.
How much can I save with a Chicago holiday package?
If you book a package deal on Expedia, you can save as much as $583*.
Can I choose my airline with a Chicago Expedia holiday package?
Look around our universal database of more than 550 airline partners and 1,000,000 properties worldwide. Too many to select from? Don’t worry — we’ll help you decide!
Do I lose money if I change my mind after I have booked my Chicago holiday package?
If you change your plans, we will honour your cancellation request on almost all bookings with no extra fee.
What are the best places to visit in Chicago?
Preparing for your trip to Chicago? Need some info about what to see when you arrive? That’s where we can assist! Take it from us, your bucket list will be heaps shorter after a trip to Chicago! Famed attractions like the Art Institute of Chicago and Willis Tower should be some of your first ports of call. The McCormick Place and the University of Illinois Chicago also draw in crowds of travellers from all across the globe. You’re going to find yourself surrounded by terrific things to do and see, including Navy Pier and the Lincoln Park Zoo. If you’re dying to get the most out of your stay, also check out Lincoln Park and the Chicago Cultural Centre. Millennium Park is an oasis amid the bustle of everyday life. Pull off your shoes and feel the cool grass beneath your feet or simply lie on your back and spot shapes in the clouds. Adventurers in this destination have heaps of options. Those who are a little queasy around heights might want to look away, but anyone who’s curious about skyscrapers can’t miss John Hancock Centre. Towering high above the ground, it’s a beloved fixture of the area’s skyline. Still have some time on your hands? Want to catch a sunrise among some spectacular scenery? Skydeck Ledge boasts glorious views that deserve to be photographed.
What are the most popular activities for a Chicago holiday?
When we hark back to our travels, we usually remember experiences rather than our swish hotel room and its view of the pool. Are you ready to create some new travel memories? Your trip to Chicago is about to get a lot more exciting. There are heaps of activities available, such as:To check out all the activities on offer, head to our Chicago things to do page.
What types of accommodation options are available in Chicago?
With no less than 165 accommodation in Chicago, finding a place to stay won’t be difficult. But why wait around? Book now via Expedia and kick-start your next cheap holiday or luxury getaway. Begin the quest for a dreamy Chicago base by looking into the latest offers at the Chicago Premier Suites (540 N State Street) and The Peninsula Chicago (108 East Superior Street). Alternatively, the Trump International Hotel & Tower Chicago (401 N Wabash Ave) and the Old Chicago Inn (3222 N Sheffield Ave) are two properties well worth investigating if you’re travelling on the cheap. If you’d rather stay nearby the Art Institute of Chicago, The Langham, Chicago and the JW Marriott Chicago are excellent options.
Is there an airport in Chicago?
We know the airport won’t be the most memorable moment of your holiday, but there’s nothing like the excitement of knowing that your well-deserved trip to Chicago is just a flight away! Once you unbuckle your seatbelt at Midway International Airport (MDW), you’ll be 9 miles from the heart of town.