Bolingbrook Vacations

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Find the Best Bolingbrook Vacation Packages

Bolingbrook 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 O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is AED 750 per night from Mar 1 to Mar 2
AED 750
AED 880 total
1 Mar - 2 Mar
includes taxes & fees
8.2/10 Very Good! (2,216 reviews)
Very comfortable room. Quiet. Blackout curtains. Nice size bathroom

Reviewed on 8 February 2026

Hilton Chicago O'Hare Airport
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! (2,613 reviews)
Outdated rooms and our heater stopped working overnight and the temp fell to 60's which felt freezing given it was zero outside with snow flurries But Matt the maintenance guy came quickly at 6 am thankfully and got it back up and running. Other than that, a truly beautiful hotel and the restaurant ...

Reviewed on 8 February 2026

Hilton Chicago
See all 4,526 properties in Bolingbrook
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 Bolingbrook

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 theater 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 Bolingbrook that have flexible change policies?
When it comes to traveling these days, flexibility is a must. That's why we have a "No change fee" filter to help you find flexible, low-cost tickets to Bolingbrook. It's on the left-hand side of your screen directly under the "Flexible change policies" heading.
Which airlines fly to Bolingbrook?
Whether you'd like to sit in first class or cut costs in economy, these popular carriers will fly you to or near Bolingbrook:

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

How can I find cheap tickets to Bolingbrook?
Book well ahead of time, fly to or from nearby airports, use miles or points — there are plenty of ways! One more is to make use of Expedia's "flexible dates" feature. Search for a Bolingbrook flight, then compare the prices for nearby dates. In the last seven days, the best price for a flight to Bolingbrook was .
How much is a flight to Bolingbrook?
In the last seven days, round-trip airfares to Bolingbrook sold for as low as and peaked at . For one-way trips out of (), the lowest price during this time was just .
What are the most popular airports to fly into in Bolingbrook?
Depending on which carrier you travel with and departure city, one of these popular airports will be your gateway to Bolingbrook:

  • 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 Bolingbrook?
If you can be flexible with what date you jet off to Bolingbrook, leave early in the week. The most affordable day to take off is generally Tuesday, closely followed by Monday. Saturday is typically the costliest day, with a lot of people choosing to fly on the weekend.
How much is a plane ticket to Bolingbrook?
In the last seven days, journeys to Bolingbrook ranged between and . Prices depend on a number of things, particularly the departure time, seating class, airline and how early you make your booking.
What months are the cheapest to book a flight to Bolingbrook?
February is the best month to book your Bolingbrook getaway. Fares are at a premium throughout December, so avoid this time if possible.
How long is a flight to Bolingbrook?
It could be a couple of hours or more — it mostly depends on which part of the USA you're coming from. The average flight times for these well-known domestic routes to Bolingbrook will give you a good idea of what to expect:

  • 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