Chicago Vacations from $295

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Your Chicago getaway

With a multitude of well-known landmarks and vibrant neighborhoods to explore, Chicago promises an unforgettable vacation. Discover accommodations in downtown Chicago, offering access to top-tier dining, cultural hotspots, and captivating entertainment. From Millennium ParkOpens in a new window to the Art Institute of ChicagoOpens in a new window, design your perfect itinerary and make unforgettable memories with ease through Expedia.

The Latest Chicago vacation packages

Price found within the past 48 hours. Click for updated prices.
The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Save 100% on your flight
Price was $477, price is now $295 per person
$295
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (146 reviews)
Popular with drunks that party way past reasonable quiet hours.

Reviewed on Sep 27, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $588, price is now $309 per person
$309
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
The hotel staff were friendly and the room was quiet and clean. we had an issue with the room safe and it was fixed right away. the location was excellent for walking to all the attractions we wanted to see. Overall we were very happy with our stay.

Reviewed on Oct 2, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $729, price is now $391 per person
$391
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Quiet comfortable room, great area, stunning evening view from roof deck.

Reviewed on Oct 2, 2025

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $609, price is now $387 per person
$387
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,922 reviews)
The hotel is well located but a bit dated overall. The room was all right but it was 77F when I arrived and the AC was not keeping up with the sun. Breakfast service was DMV level terrible. I had better experiences at IHOP.

Reviewed on Oct 1, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $878, price is now $565 per person
$565
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
Best place to stay when facing an early morning flight!

Reviewed on Oct 1, 2025

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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 showing 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

Discover the most popular places to visit in Chicago

Wrigley Field featuring cbd, a sporting event and a city

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 night scenes, a city and signage

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.

Michigan Avenue
Navy Pier featuring a sunset and rides

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

$49
per adult
96% of travellers recommend
Architecture River Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

$45
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

$45
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago

Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,258 reviews)
"Love this place"

Reviewed on Oct 2, 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$192 nightly
The price is $226 total per night from Nov 2 to Nov 3
$226 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (5,023 reviews)
"Clean , a great location and the amenities are awesome"

Reviewed on Oct 1, 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $176 total per night from Nov 2 to Nov 3
$176 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (3,002 reviews)
"The staff were super helpful. Great location, we were able to walk to the navy pier, the bean, and all the stores on Michigan Avenue! Only downside was the pool was closed but we were told that ahead of time!"

Reviewed on Oct 2, 2025

Hilton Chicago/Magnificent Mile Suites
See all 5,363 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.

Chicago Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
2,720,500
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Chicago Riverwalk, John G. Shedd Aquarium and Art Institute of Chicago

Why visit Chicago

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Frequently asked questions

How much does a Chicago vacation package cost?
You'll find cheap prices from $295 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 vacation to Chicago costs.
What are the cheapest months to go to Chicago?
You can generally find lower prices and greater availability in December, January and February. Explore our cheap Chicago vacation packages and you could score some excellent off-season deals.
How many days is enough for Chicago?
To fully enjoy a Chicago vacation, we suggest staying for 2 days. Divide your time between visiting Shedd Aquarium, Chicago Theatre and other leading sights, on top of exploring neighborhoods like Central Chicago and Magnificent Mile. If you've got some time to spare, include a day trip or tour in your Chicago vacation itinerary.
Is it worth booking a vacation package to Chicago?
Chicago has everything you need for an awesome break — culture, views and dining are just the start. Whether you want to visit sights such as Millennium Park and Art Institute of Chicago, or venture off the beaten track, you'll find plenty to explore on your Chicago vacation.
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 vacation package well in advance.
Is it cheaper to book a Chicago vacation as a package?
Expedia vacation 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 customized Chicago vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation 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 your dates: What you'd like to do in Chicago and your favorite season can help you decide when to go.
  2. Set your budget: Consider costs like flights, food and transportation when calculating how much to put aside for your trip to Chicago. Then, pick a property that works with your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Organize your Chicago escape with our trip planning tool: Look for and book accommodations and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Chicago together.
  4. Decide how long to go for: Now that you're up to speed on Chicago, you can work out the ideal length of your vacation. Pull together a draft itinerary and give yourself enough time to cover everything you want to do.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Chicago vacation package.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some awesome things to do in Chicago. Book tickets or make reservations in advance to save time and avoid the hassle of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Chicago vacation packages?
Jet off on your dream getaway to Chicago with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for the next payday — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snag great deals before they disappear.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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