Chicago Trip

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Discover architectural marvels and vibrant culture in Chicago

Chicago is a captivating city that blends urban splendor with rich culture and history. Situated on the shores of Lake Michigan, Chicago offers a stunning skyline adorned with towering skyscrapers. The city is renowned for its vibrant theater scene, awe-inspiring architecture, and world-class museums. Visitors can immersey themselves in art and history, explore iconic monuments, and indulge in endless entertainment options. Downtown Chicago is a must-visit, offering a bustling atmosphere, picturesque scenery, and fantastic shopping opportunities. A trip to Chicago will leave you enchanted by its unique charm and unforgettable experiences.

Where to stay in Chicago

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

Explore the best places to visit and stay in Chicago

When it comes to exploring Chicago and its vicinity, you'll be captivated by the diversity and excitement that each area has to offer. Here are some of the must-visit neighborhoods:

  • Downtown Chicago: This vibrant area is the heart of the city, boasting a stunning skyline filled with skyscrapers. Immerse yourself in the thriving theater scene, marvel at the architectural wonders, and explore world-class museums and art galleries. Don't miss the iconic monuments and indulge in some retail therapy amidst the bustling shopping districts.
  • Magnificent Mile: Located on Michigan Avenue, this upscale neighborhood is famous for its luxurious shopping experience. Stroll along the mile-long stretch and be amazed by the grandeur of the historic buildings, while enjoying the theater performances and admiring breathtaking art collections.
  • The Loop: Situated in the heart of downtown, The Loop is known for its iconic "L" train loop. Explore the vibrant theater district, discover impressive architecture, visit renowned museums, and soak in the lively atmosphere. Don't forget to take in the stunning scenery and enjoy the shopping opportunities.

Each area in Chicago offers a unique blend of urban charm, cultural treasures, and exciting experiences that will make your trip unforgettable.

Experience the top activities and must-see sights in Chicago

Chicago is a vibrant city filled with urban charm, towering skyscrapers, world-class theaters, stunning architecture, captivating museums, breathtaking art, iconic monuments, lively entertainment, picturesque scenery, and a shopping paradise.

  • McCormick Place: Immerse yourself in the urban atmosphere of Chicago at this event and conference venue. Marvel at the skyscrapers, indulge in theatrical performances, explore architectural wonders, delve into museums, appreciate art, visit monuments, enjoy entertainment, and indulge in shopping.
  • Wrigley Field: Experience the electric energy of this sports facility and stadium. Witness the towering skyscrapers surrounding the field, enjoy theatrical performances, admire architectural features, explore nearby museums, appreciate art, visit monuments, revel in entertainment, and indulge in shopping.
  • Navy Pier: Delight in the charm of this jetty pier. Be enchanted by the urban skyline and skyscrapers, immerse in theatrical experiences, admire architectural gems, explore museums, appreciate art, visit monuments, revel in entertainment, soak in the scenic views, and indulge in shopping.

Discover the flavours of Chicago

Chicago is a food lover's paradise, offering a wide range of local cuisine and unique dishes. From deep-dish pizza to Chicago-style hot dogs, the city is known for its iconic dishes. You can also indulge in delicious ethnic cuisines, such as Mexican, Italian, and Polish, which reflect the diverse cultural heritage of the city. Don't forget to try the famous Chicago-style popcorn, a delightful combination of caramel and cheese flavours.

When it comes to dining experiences, Chicago has a vibrant food scene with numerous top-rated restaurants. A must-visit is Alinea, a three-Michelin-star restaurant that offers a multi-sensory dining experience with innovative and artistic dishes. For a taste of Chicago's history, head to The Berghoff, a classic German-American restaurant that has been serving traditional dishes since 1898. Other notable restaurants include Girl & the Goat, known for its creative small plates, and Lou Malnati's Pizzeria, where you can savor the city's famous deep-dish pizza.

Best time to go to Chicago

Chicago (and vicinity) boasts a year-around average temperature of 10.8°C, peaking at 24.4°C in July, its warmest month, and dipping to an average low of -4.0°C in January, the coolest. Rainfall averages at 82.8mm annually, with May seeing the heaviest showers and February being the driest month.

Monthcalendar iconTemperature (Celcius)temperature iconRainfall (mm)rain icon
January-4.052.3
February-1.849.3
March3.869.1
April10.392.5
May16.1104.9
June21.7103.1
July24.4101.9
August23.4101.3
September19.184.1
October12.482.3
November5.386.9
December-1.765.3

Top reasons to visit Chicago

  • Captivating Cityscape: Chicago's skyline, adorned with towering skyscrapers, creates a mesmerizing urban splendor.
  • Rich Cultural Scene: The city offers a vibrant theater scene, captivating museums, and a thriving art and history heritage.
  • Breathtaking Architecture: Explore iconic architectural wonders that make Chicago famous, showcasing stunning designs and structures.
  • Picturesque Scenery: Situated on the shores of Lake Michigan, Chicago offers scenic views and a bustling atmosphere in its downtown area.
  • Fantastic Shopping Opportunities: Indulge in a shopping paradise with bustling shopping districts, upscale neighborhoods, and a luxurious shopping experience along the Magnificent Mile.

The Chicago info point: What you need to know

Category
Details
What is Chicago known for?Architecture, Deep-dish pizza, Blues music
Most popular month?June, July, August
Length of Stay3-5 days
WeatherCold winters, hot summers
Don't missThe Art Institute of Chicago, Millennium Park, Navy Pier
CuisineChicago-style hot dogs, Italian beef sandwiches, Garrett Popcorn
Where to goThe Magnificent Mile, Navy Pier, Grant Park

Find the Best Chicago Vacation Packages

Chicago Hotel Deals

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 ₹8,876 per night from 23 Dec to 24 Dec
₹8,876
₹10,420 total
includes taxes & fees
23 Dec - 24 Dec
7.8/10 Good! (8,257 reviews)
"For the price the property was great! The room we stayed in looked like it was recently done and was huge with nice beds and redone bathroom. You could tell the age of the building though. Many rooms on our floor were padlocked - perhaps just hadn't been refinished (hotel is huge so perhaps not all ..."

Reviewed on 19 Dec 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is ₹7,912 per night from 20 Jan to 21 Jan
₹7,912
₹9,288 total
includes taxes & fees
20 Jan - 21 Jan 2025
8.6/10 Excellent! (3,620 reviews)
"This hotel is great! The staff helped us check in early and provided us with a river view room. My friend and I were both very happy^^ Although it’s close to the busy road, the room is not noisy. The location of the hotel is also very good, making our travel convenient."

Reviewed on 17 Dec 2024

River Hotel
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₹12,549 per night from 5 Jan to 6 Jan
₹12,549
₹17,227 total
includes taxes & fees
5 Jan - 6 Jan 2025
9/10 Wonderful! (3,037 reviews)
"I loved my stay. One of the best hotels in the city."

Reviewed on 18 Dec 2024

Hyatt Regency 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.

Frequently asked questions

How much does a Chicago holiday package cost?
You’ll find cheap prices 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.
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.

💰 How to find great deals on package in Chicago

  • Combine your flights with hotels or car rentals to save money on Expedia.
  • Take advantage of Expedia's Rewards program to collect points and save money on your Chicago trip.
  • Use the search filters on Expedia to find the perfect accommodation within your budget.
  • Consider traveling during the off-peak season, typically from November to February, for better package deals.
  • Check for special promotions and discounts on Expedia for Chicago attractions and activities.
  • Book your package deal in advance to secure the best prices and availability on Expedia.
  • Consider bundling your Chicago package with nearby attractions like Milwaukee or Indianapolis for a more diverse trip.
  • Don't forget to check the weather forecast for Chicago during your travel dates to pack accordingly.
  • Read reviews and compare different package deals on Expedia to ensure you're getting the best value for your money.
  • Stay flexible with your travel dates to take advantage of any last-minute deals on Expedia.

Discover the most popular places to visit in Chicago

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