Chicago Holidays

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    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Chicago

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
30 Oct - 3 Nov
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
The location was good. Staff was friendly. It was clean. But it was hard to enjoy time in the room because of the TV. They had horrible cable with nothing on, and it wasn’t a smart tv so we couldn’t log into any of our streaming services or even stream from our phones to the tv. We had to go out and buy a firestick.

Reviewed on 10 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Oct - 3 Nov
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
I feel like Europe. Very nice

Reviewed on 11 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
30 Oct - 3 Nov
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Gorgeous hotel. Hotel staff in all areas were extremely professional and helpful to include front desk, concierge, bar tenders, hostess and cleaning crew.

Reviewed on 10 Aug 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
per person
30 Oct - 3 Nov
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Restaurant had good breakfast

Reviewed on 9 Aug 2025

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
per person
30 Oct - 3 Nov
found 3 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,005 reviews)
Comfortable bed and walkable but rooms can be noisy for outside noises

Reviewed on 10 Aug 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 which includes 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

Top hotels in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €253 per night from 7 Sept to 8 Sept
€253
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (8,939 reviews)
Vintage hotel in amazing location
"This is a beautiful old hotel in a great location in very good to excellent condition. The A/C worked fine, the bed was comfortable, and we had a lovely view of the lake and the fireworks at Navy Pier. The location, right across from Buckingham Fountain, is great. My partner and I thought that the ..."

Reviewed on 10 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €196 per night from 21 Aug to 22 Aug
€196
21 Aug - 22 Aug
includes taxes & fees
8.2/10 Very Good! (1,836 reviews)
"The property if beautiful and historic. The main room is incredible. The rooms are well taken care of, you can just tell they are a little dated with a slight smell. I would definitely stay here again."

Reviewed on 8 Aug 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €155 per night from 24 Aug to 25 Aug
€155
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (3,657 reviews)
"Great rooms, comfortable, walking distance to anywhere you’d want to go."

Reviewed on 10 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 5,407 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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing street scenes, signage and night scenes

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.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Chicago

River tour boat in Chicago

Architecture River Tour

€36
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago

Frequently asked questions

How much does a Chicago holiday package cost?
You'll find cheap prices from €626 on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Chicago costs.
What are the cheapest months to go to Chicago?
December, January and February are the best times to look for cheap Chicago holiday packages. Opting to travel in quieter periods means you'll typically find lower prices on accommodation and flights.
How many days is enough for Chicago?
To fully enjoy a Chicago holiday, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue, Chicago Riverwalk and other well-known attractions, on top of experiencing neighbourhoods like Central Chicago and Near North Side. If you've got some spare time, include a day trip or tour in your Chicago holiday itinerary.
Is it worth booking a holiday package to Chicago?
Chicago has everything you need for a fantastic trip — views, dining and culture are just the start. Whether you want to visit attractions like Navy Pier and Soldier Field, or take the road less traveled, you'll find plenty to do on your Chicago holiday.
How to find the best Chicago package deals?
Use Expedia's filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Chicago holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the freedom to create a customised Chicago holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Chicago?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.
How to plan a trip to Chicago?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chicago.
  2. Set a budget: Factor in costs like flights, transportation and food when working out how much to put aside for your trip to Chicago. Then, choose a property that suits your budget, whether that's an affordable stay or a swankier getaway.
  3. Work out your trip length: Consider how long you'd like to spend discovering Chicago. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chicago holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.