Cheap Vacations in Downtown Chicago

Choose two or more items and save on your trip:
Choose two or more items and save on your trip:

Downtown Chicago vacations

Swissotel - Chicago
The Langham, Chicago
The Whitehall Hotel
Fairmont Chicago at Millennium Park
Hotel Lincoln, part of JdV by Hyatt
InterContinental Chicago Magnificent Mile, an IHG Hotel
Chicago Marriott Downtown Magnificent Mile
Moxy Chicago Downtown
Le Méridien Essex Chicago
Congress Plaza Hotel

3-night Downtown Chicago vacations

Chicago Athletic Association, part of Hyatt
Viceroy Chicago
Hilton Garden Inn Chicago Downtown Riverwalk
River Hotel
Fairmont Chicago at Millennium Park
Hotel Lincoln, part of JdV by Hyatt
Chicago Marriott Downtown Magnificent Mile
Le Méridien Essex Chicago
Thompson Chicago
Swissotel - Chicago
Trump International Hotel & Tower Chicago
Hyatt Centric Chicago Magnificent Mile

4-night Downtown Chicago vacations

The Langham, Chicago
Hotel Lincoln, part of JdV by Hyatt
Fairmont Chicago at Millennium Park
Trump International Hotel & Tower Chicago
Congress Plaza Hotel
Hyatt Centric Chicago Magnificent Mile
Chicago Marriott Downtown Magnificent Mile
InterContinental Chicago Magnificent Mile, an IHG Hotel
Thompson Chicago
Best Western Grant Park Hotel
Eurostars Magnificent Mile
The Talbott Hotel, part of JdV by Hyatt

5-night Downtown Chicago vacations

Congress Plaza Hotel
Sofitel Chicago Magnificent Mile
Club Quarters Hotel, Wacker at Michigan
River Hotel
Club Quarters Hotel, Central Loop
Central Loop Hotel
Swissotel - Chicago
Fairmont Chicago at Millennium Park
Hotel Lincoln, part of JdV by Hyatt
Chicago Marriott Downtown Magnificent Mile
Le Méridien Essex Chicago
Trump International Hotel & Tower Chicago

Where is Downtown Chicago?

Always wanted to visit Downtown Chicago? Purchase that low-cost flight already and start getting excited about your next cheap-yet-chic getaway!

The population of Chicago is about 2,695,600.

Cheap Things to do in Downtown Chicago

Flights and hotels booked — check! Bag packed — check! Days brimming with free things to do in or near Downtown Chicago — you know it! Our list below will help make sure that your getaway is kind on your budget.

  • The Driehaus Museum, the Fine Arts Building, the National Museum of Mexican Art and the Money Museum are great for those visitors with inquiring minds and limited funds. The best part of spending an hour or so there is that they won't charge you anything!
  • Taking in arts and cultural events is a great way to get a real sense of the area. Check out the upcoming programs at the Cloud Gate, the Museum of Contemporary Photography, the Crown Fountain and the ArchiTech Gallery to discover some awesome free shows.
  • Give boredom the boot without ruining your budget at Northerly Island Park. It ought to be the first place you visit if you're after some outdoor thrills.
  • Cost-conscious history buffs will want to add the University of Illinois Chicago, the Merchandise Mart, the Buckingham Fountain and Tribune Tower to their vacation schedules. These time-honored sites also offer superb photo ops!
  • Go to your choice of Mariano Plaza and Chicago Riverwalk and chat to the locals about the leading (and cheapest) attractions, sights and dining places. These well-liked areas are worth exploring.

Cheap Downtown Chicago Vacation Package Deals

Take note, at CheapTickets cheap really doesn't have to mean nasty. Even though we're madly cost conscious, we won't make trade-offs on quality and comfort.

Customize your frugal adventure by picking and choosing from more than 500 airline partners and 500,000 global properties. To access savings of up to $287, simply combine your booking with a hotel and flight package.

We're not joking when we say we're dedicated to saving you a pretty penny. If you come across a cheaper price within 48 hours of securing your package, we'll match that price and refund you the difference. It's our Price Guarantee!

Get CheapCash

Sometimes it can be difficult parting with your pennies that's why we created our simple rewards program. Just for booking your flights, you'll have cash savings to use toward your next eligible CheapTickets hotel booking.

How easy is CheapCash? Simply sign up for a new account free of charge or log in to your existing one, join the program, and you'll automatically get access to thrifty bonus offers and perks — and of course you'll accrue savings on your eligible bookings. It's minimal effort for maximum rewards!

Cheap Car Rentals in Downtown Chicago

Trust us cheapster — if you're using taxis to get from one place to another on your getaway, it doesn't take much time to rack up a massive bill. So, why not consider renting a car for your trip to Downtown Chicago? Not only will it be easier on your wallet, you'll also be able to go where you want, when you want!

Cheap Hotels in Downtown Chicago

There's no need to fritter away most of your budget on someplace to stay. You'll find some wonderful and cheap options, such as The St. Clair Hotel (162 East Ontario Street, Chicago 60611, IL) and the HI Chicago (24 East Congress Parkway, Chicago 60605, IL).

Flight deals to Downtown Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Top rated hotels for your Downtown Chicago vacation

Don't see what you're looking for?
See all available properties in Downtown Chicago
View all properties
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.