Chicago Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AED 148 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

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 AED 544 per night from Feb 13 to Feb 14
AED 544
AED 638 total
13 Feb - 14 Feb
includes taxes & fees
8/10 Very Good! (9,853 reviews)
Friendly staff. Clean room.

Reviewed on 5 February 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AED 509 per night from Feb 21 to Feb 22
AED 509
AED 705 total
21 Feb - 22 Feb
includes taxes & fees
8.4/10 Very Good! (2,610 reviews)
Good

Reviewed on 7 February 2026

Hilton 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
Fully refundableReserve now, pay when you stay
The price is AED 376 per night from Feb 22 to Feb 23
AED 376
AED 442 total
22 Feb - 23 Feb
includes taxes & fees
8.4/10 Very Good! (5,637 reviews)
Yes room was spotless

Reviewed on 4 February 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 5,628 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.

Discover the most popular places to visit in Chicago

Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(332 reviews)

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

4.5/5(4,870 reviews)

With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Navy Pier
Chicago Riverwalk which includes a city, a bay or harbor and a river or creek

Chicago Riverwalk

4.5/5(1,535 reviews)

After visiting Chicago Riverwalk, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront in this vibrant area, or check out its top-notch restaurants.

Chicago Riverwalk

Frequently asked questions

How do I find cheap flights to Chicago that have flexible change policies?
Search for cheap fares to Chicago, then mark the "No change fee" box below the "Flexible change policies" filter. It's as easy as that. We get that travel plans can change and flexibility is important, so you can book with confidence with Expedia.
Which airlines fly to Chicago?
When it's time for your next adventure, these reputable airlines will make escaping to Chicago nice and simple:

  • United Airlines - 13,009 flights to or near Chicago each month, including 13,005 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 10,036 flights to or near Chicago each month, including 10,036 flights to O'Hare Intl. Airport (ORD) per month.

How can I find cheap tickets to Chicago?
One of the easiest ways to nab cheap tickets to Chicago is to be flexible with your dates. Search for your flights, then click "flexible dates" at the top of your results. It'll bring up the cheapest prices for nearby days. The lowest price for a flight to Chicago in the last seven days was . Booking well ahead will generally help you pick up an even bigger bargain.
How much is a flight to Chicago?
If you were traveling one way from (), you could've locked in an affordable ticket for in the last seven days. Round-trip flights to Chicago ranged from only to during this same period.
What are the most popular airports to fly into in Chicago?
Depending on your budget, carrier and place of departure, one of these top airports will be your gateway to Chicago:

  • O'Hare Intl. Airport (ORD) - 26,484 flights per month.
  • Midway Intl. Airport (MDW) - 6,439 flights per month.

When is the cheapest time to fly to Chicago?
Taking off on a Tuesday, followed by a Monday, is usually the best way to land the cheapest airfare. Avoid the weekends if you can, because Saturday is typically the costliest day. Spend the funds you saved living it up in Chicago instead!
How much is a plane ticket to Chicago?
In the last seven days, plane fares to Chicago ranged between and . Prices usually rise as your travel date nears, so grab an awesome deal today.
What months are the cheapest to book a flight to Chicago?
February is the perfect month to bag a terrific deal to Chicago. Be aware that the priciest time to purchase tickets in the U.S. Isn't the middle of summer, but the festive month of December.
How long is a flight to Chicago?
Whether or not you'll have time to read one chapter of your book or a few depends on where you're coming from. To give you a rough idea, here are the average flight times for some busy domestic routes to Chicago:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 37 minutes
  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 34 minutes
  • Phoenix, AZ (PHX-Sky Harbor Intl.) to O'Hare Intl. Airport (ORD) - 3 hours and 17 minutes

What are the best things to do in Chicago?

  • Overflowing with atmosphere and culture, Naperville is a fantastic starting point for your Chicago vacation. Tour renowned attractions like Centennial Beach, hit up the shops or wine and dine your way around some of this city's inviting bars and restaurants. What you decide to do is up to you!
  • When you're organizing what to do on your escape, keep in mind that Naperville is known for its humid continental climate. It's a good idea to check the weather conditions before you jet off so you can better understand what to expect.
  • Approximately 18 kilometers to the north of Naperville, Carol Stream also deserves a place on your itinerary. Well-known sights in this city include Xtreme Trampolines — be sure to check it out.