Chicago Vacations

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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
A busy city street with tall buildings, a bus, and cars.

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 SAR 512 per night from Jun 29 to Jun 30
SAR 512
SAR 609 total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,132 reviews)
"The hotel is a bit run down, but my room was very clean. The breakfast was good, although it is not included, and for some reason I thought it was. The receptionist was amazing. She was very kind and allowed me to check in early, which I really appreciated. The location is also excellent. I’m giving ..."

Reviewed on 26 June 2026

Congress Plaza Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is SAR 478 per night from Jun 28 to Jun 29
SAR 478
SAR 544 total
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,731 reviews)
"Very convenient ... close to Ohare, free shuttle."

Reviewed on 27 June 2026

Hyatt Regency O'Hare Chicago
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
The price is SAR 619 per night from Jul 5 to Jul 6
SAR 619
SAR 736 total
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (4,464 reviews)
"Location was great. Everything at the hotel from checkin to chef out was very smooth."

Reviewed on 26 June 2026

Hilton Chicago/Magnificent Mile Suites
See all 5,355 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.

Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/5 (11,704 reviews)
Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."
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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.