Chicago Trip

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Top Chicago Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Trump International Hotel & Tower Chicago
Hotel Riu Plaza Chicago
Pendry Chicago
Hilton Grand Vacations Club Chicago Magnificent Mile

Where to stay in Chicago

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

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

💰 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.

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

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 ₹11,204 per night from 3 Nov to 4 Nov
₹11,204
₹13,153 total
3 Nov - 4 Nov
includes taxes & fees
8/10 Very Good! (9,412 reviews)
"The person at the registration desk directed me to the wrong tower for my room. He even wrote it on the key holder. Otherwise hotel is fine. Excellent location near the Art Institute, parks and lakefront."

Reviewed on 14 Oct 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₹5,910 per night from 11 Nov to 12 Nov
₹5,910
₹8,484 total
11 Nov - 12 Nov
includes taxes & fees
7.8/10 Good! (2,460 reviews)
"Wonderful hotel. First time staying at a place like this. Ended up having the quad room to myself for both nights I was there. Will definitely try to book there again if traveling solo."

Reviewed on 13 Oct 2025

Freehand Chicago
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
The price is ₹12,616 per night from 16 Nov to 17 Nov
₹12,616
₹14,810 total
16 Nov - 17 Nov
includes taxes & fees
8.4/10 Very Good! (5,096 reviews)
"Great location, clean modern rooms, friendly staff"

Reviewed on 12 Oct 2025

Embassy Suites by Hilton Chicago Downtown River North
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

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