Cheap Chicago Vacations

Chicago

Your Chicago vacation

From food to theater and Lake Michigan to the Loop, Chicago is home to some equally big names. But you don't need to fly in on Obama's Air Force One or have pockets as deep as Oprah to be able to experience a Chicago vacation at its fullest. Take a stroll down the Magnificent Mile, catch a Cubs game at Wrigley Field, and soak up the waterfront culture of the Second City.

Before you rush to Millennium Park, allow CheapTickets to help you with the planning. We'll share the city's top highlights that will blow your mind -- without blowing your budget.

Cheap Vacation Packages

Cheap Chicago Vacation Packages

Congress Plaza Hotel at Grant Park

3 stars
3.3 / 5 1087 reviews
With its neon-red sign standing out against the Chicago skyline, its vaulted Italianate ceilings, and glimmering 'Gold Room' banquet hall, the Congress Plaza Hotel makes an imposing first impression. Once known as the "Home of Presidents" due to its popularity with both Roosevelt's, Woodrow Wilson and Richard Nixon, it's been operating since 1893. Valet dry-cleaning and barber services of yesteryear sit side-by-side with modern amenities like audiovisual tech for business meetings and a 24-hour fitness center. On-site eating options are globally diverse (Rafael's Steakhouse) and come straight from the griddle in the morning (Gazebo Restaurant). In the evenings, settle into a leather back armchair with a bourbon, or take your shots at the dartboard in the Congress Lounge, where both business users and vacationers gather for some much-needed R&R. Key facts871 guestrooms36 suites23 meeting/event rooms2 restaurants: Rafael's Steakhouse, Gazebo RestaurantCongress Lounge & BarGift shopBarber shop24-hour gymValet dry cleaning/shoeshineSmoking rooms available on request NeighborhoodAcross the street from Grant Park and the famous Buckingham Fountain, Congress Plaza rests on the main thoroughfare and shopping mecca of Michigan Avenue, aka, the Magnificent Mile. The hotel is walking distance from world-renowned institutions like the Art Institute of Chicago, Shedd Aquarium, and the fascinating Field Museum. Found on the banks of Lake Michigan, the Field Museum is the home of "Sue," the largest and most complete Tyrannosaurus Rex skeleton ever discovered, as well as a life-size Maori meeting house. Hints and tipsThe Congress is frequently nicknamed 'the most haunted hotel in Chicago,' and budding paranormal detectives should request a room in the oldest part of the building, the South Tower, for the 'highest chance' of ghostly activity.Be on the lookout for characters like notorious murder victim Peg Leg Johnny, or test your courage near the 12th floor room which was allegedly closed down due to paranormal activity.
Value Save 10% on your stay
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $116

Club Quarters Central Loop

3 stars
4.1 / 5 528 reviews
Business traveler headquarters in Chicago's LoopThe Club Quarters Central Loop hotel might be mistaken for an office building with its subdued presence. A black awning marks this discrete spot and lends a sense of privacy. The hotel targets business travelers whose work brings them to the financial district and plays host to leisure travelers who want easy access to downtown attractions. Guests find great value for the location, price and attentive service, including a 24-hour concierge. The Club Quarters Central Loop hotel is within walking distance of several of Chicago's major attractions. Highlights Minutes from Michigan Avenue 24-hour concierge service Free high-speed wireless Internet throughout the hotel Elephant & Castle Pub and Restaurant next door RoomsThe clean and comfortable rooms at the Club Quarters Central Loop hotel keep the professional’s needs in mind. Ergonomic chairs and task lighting ease late work nights, while pillow-top mattress dressed in premium linens promise a refreshing night of sleep. Bookshelves display dictionaries and almanacs for a welcome scholarly touch. All rooms have complimentary wireless Internet access. FeaturesThe amenities at the Club Quarters Central Loop hotel are designed to keep guests productive. Find free high-speed wireless Internet access throughout the hotel, free use of a computer and printer, and five meeting rooms. Travelers looking to relax visit the restaurant and bar next door, exercise in the fitness room or lounge in the Private Club Room (Club Quarters members only) with complimentary coffee, tea, newspapers, magazines and games.Free, chilled bottled water is available on each floor. Transportation O’Hare International Airport (15.6 mi/25.1 km) Midway Airport (8.9 mi/14.3 km) Blue Line (Jackson/Dearborn) (0.1 mi/0.2 km) Orange Line (Quincy/Wells) (0.1 mi/0.2 km) McCormick Place Convention Center (2.1 mi/3.3 km) Attractions Board of Trade (0.1 mi/0.2 km) Theater district (0.2 mi/0.3 km) Willis (formerly Sears) Tower (0.2 mi/0.4 km) Symphony Center (0.3 mi/0.5 km) Chicago Mercantile Exchange (0.3 mi/0.5 km) The Art Institute of Chicago (0.4 mi/0.6 km)
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $77

River Hotel

3 stars
3.9 / 5 354 reviews
Perfect location at the top of the Magnificent mileAs locations go, this Wacker Drive hotel couldn't do better, occupying prime riverfront space in the historical Mather Tower off the Magnificent Mile. The landmark River Hotel has kept up with the times, especially when it comes to environmental impact. Its LEED-registered building and Green Power Partner utilizes low-flow showerheads and participates in recycling programs. For what it may lack in luxury and size, the hotel scores on points like casual ambiance, simplicity and value. Highlights LEED-registered hotel with green design and practicesKitchenettes available, plus free chilled, purified bottled waterDelivery from select neighborhood restaurants Bella Bacino's Italian Bistro & PizzeriaFree high-speed wireless Internet access throughout the hotel RoomsWell-kept, comfortable rooms at the River Hotel offer the no-frills traveler twin, full, premium queen and king beds, plus work station. Some rooms are equipped with kitchenettes, and corporate apartments are available for professionals seeking accommodations for longer than a month.   FeaturesNot every professional has an expense account and travel-related costs can really add up -- lodging, food and transport to name a few. For the conservative business traveler, the River Hotel offers a great value with special perks like free wireless Internet access and complimentary chilled, purified bottled water. The River Hotel has a convenient location in Chicago, steps from the Magnificent Mile, Tribune Tower, Millennium Park and the Loop for business travelers.Other features include a 24-hour concierge, and fitness room. Bella Bacinos, a casual Italian-American trattoria, is open for breakfast, lunch and dinner. Valet and self-parking are available for a fee. TransportationO’Hare International Airport (15.6 mi/25.2 km)Chicago Midway Airport (9.5 mi/15.3 km)Blue Line (Clark/Lake) (0.3 mi/0.5 km)Orange Line (State/Lake) (0.2 mi/0.3 km)McCormick Place Convention Center (2.5 mi/4.1 km) AttractionsTribune Tower (0.2 mi/0.3 km)Wrigley Building (0.2 mi/0.3 km)Millennium Park (0.4 mi/0.6 km)The Magnificent Mile (0.4 mi/0.7 km)The Loop (0.5 mi/0.8 km)Board of Trade (0.7 mi/1.2 km)Chicago Mercantile Exchange (0.8 mi/1.2 km) BusinessThree meeting rooms24-hour concierge Same-day dry cleaning and laundry serviceComplimentary high-speed wireless Internet access throughout the hotel
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $94

Club Quarters Wacker at Michigan

3 stars
4.0 / 5 532 reviews
Business hotel just off the Magnificent MileThe Club Quarters Wacker at Michigan Avenue hotel attends to the needs of the business traveler. Perched at a picturesque curve of Wacker Drive near the Chicago River, the hotel treats guests to professional amenities like complimentary Wi-Fi throughout the property, free use of a computer and printer, a 24-hour member service desk and concierge and ergonomic workstations in the rooms. Leisure travelers also find its close proximity to the Magnificent Mile and other Chicago attractions irresistible. Highlights 24-hour concierge and member services desk Free high-speed Internet access throughout the hotel Prime river and skyline viewsItalian restaurant on property RoomsThe Club Quarters Wacker at Michigan Avenue hotel maintains clean, basic rooms for single day, overnight and extended stays for mostly corporate clients. Some rooms have city or river views and all are equipped with ergonomic workstations, free Wi-Fi and reference books. In some studios and suites, visitors have the added conveniences of sofa beds and kitchenettes. FeaturesThe Club Quarters Wacker at Michigan Avenue hotel offers free high-speed wireless Internet access throughout the hotel, free use of a computer and printer, and meeting space for up to 1,000 guests. Guests ready for leisure time can exercise in the fitness room, or lounge in the Private Club Room (Club Quarters members only) with complimentary coffee, tea, newspapers, magazines and games. Find free, chilled bottled water is offered on each floor. TransportationO’Hare International Airport (15.6 mi/25.1 km)Midway Airport (9.5 mi/15.3 km)Blue Line (State/Lake) (0.2 mi/0.3 km)Orange Line (State/Lake) (0.2 mi/0.3 km)McCormick Place Convention Center (2.6 mi/4.1 km) Attractions Marina City (0.1 mi/0.2 km)Chicago Cultural Center (0.3 mi/0.5 km)Millennium Park (0.4 mi/0.7 km)Michigan Avenue (0.4 mi/0.7 km)Chicago Mercantile Exchange (0.5 mi/0.8 km)Board of Trade (0.7 mi/1.2 km)Tribune Tower (0.8 mi/1.2 km)Grant Park (0.8 mi/1.3 km)The Magnificent Mile (1.1 mi/1.7 km)
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $77

The Talbott Hotel

4 stars
4.6 / 5 1175 reviews
Independently-owned and with a dedication to green practices, The Talbott Hotel has been a fixture in Chicago's Gold Coast neighborhood since 1927. The hotel mingles old-world sophistication with modern conveniences - the lobby has a cozy, open-fire warmth and the vintage-style boardrooms feature 1920s mahogany walls. Awarded the Best in Stay Award by Orbitz in 2012, the Talbott features exclusive touches like the creative Tippling Brothers cocktail menu at the Little Market Brasserie, and the knowledgeable 'Concierge Blog' on the hotel's site, setting the hotel far apart from other Chicago accommodations. Key facts149 guestroomsPets allowed (up to 50 pounds, and fees may apply)Conference and event spaces: 3 rooms, up to 200 guestsFitness centerLaundry serviceFree Wi-Fi Restaurant/bar: Little Market Brasserie NeighborhoodWith a prime location just a few blocks from Washington Square Park, Oak Street and the Magnificent Mile, The Talbott Hotel comes with easy access to shops like Bloomingdale's and Macy's, as well as the scenic Lakefront Trail on the shores of Lake Michigan. The Art Institute of Chicago is less than two miles from The Talbott's front entrance, boasting a staggering collection of over 250,000 works of art, including work by Vincent van Gogh, Claude Monet and Mary Cassatt. Hints and tipsFor privileged views of Chicago and a bit of distance from busy Delaware Street, ask for a room on the upper floors.For a more personalized stay, the Talbott Hotel's packages offer everything from the princess treatment for young daughters - including milk and cupcakes at turndown - to a $50 gift certificate  for the 900 North Michigan Shops.
Value Last Minute Deal!
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $175
Back to menu Return to top

Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Wed, Sep 10 - Sat, Sep 13 $195
Los Angeles Chicago Tue, Sep 30 - Wed, Oct 1 $269
Washington DC Chicago Wed, Oct 29 - Sat, Nov 1 $105
San Francisco Chicago Tue, Oct 21 - Thu, Oct 23 $265
Newark Chicago Wed, Oct 29 - Tue, Nov 4 $241
Atlanta Chicago Tue, Oct 21 - Fri, Oct 24 $125
Seattle Chicago Wed, Sep 24 - Tue, Sep 30 $289
Boston Chicago Tue, Sep 9 - Tue, Sep 16 $155
Dallas Chicago Sat, Sep 13 - Sat, Sep 20 $155
Denver Chicago Sat, Sep 20 - Sat, Sep 27 $145
Phoenix Chicago Tue, Oct 28 - Tue, Nov 18 $185
Orlando Chicago Tue, Sep 16 - Wed, Sep 17 $195
San Juan Chicago Sat, Sep 13 - Mon, Sep 22 $281
Mexico City Chicago Sat, Oct 18 - Sat, Nov 8 $385
Philadelphia Chicago Mon, Oct 6 - Wed, Oct 8 $318
San Diego Chicago Tue, Sep 23 - Sat, Sep 27 $290
Fort Lauderdale Chicago Wed, Oct 1 - Tue, Oct 7 $245
Las Vegas Chicago Mon, Sep 22 - Tue, Sep 23 $248
Guadalajara Chicago Tue, Sep 9 - Wed, Sep 24 $429
Tampa Chicago Wed, Sep 24 - Sat, Oct 4 $289
Houston Chicago Wed, Sep 10 - Sat, Sep 13 $173
Baltimore Chicago Tue, Oct 14 - Wed, Oct 15 $165
Honolulu Chicago Mon, Sep 15 - Fri, Sep 26 $742
Orange County Chicago Tue, Oct 21 - Wed, Oct 29 $290
Back to menu Return to top

Best time to take a vacation to Chicago

  • If you visit Chicago in the early fall you will experience the best of its weather as it retains its warm temperatures but loses the humidity of the summer months. Spring time is cooler, and it is a good time to capture those cheaper flights and hotels. The Chicago Blues Festival every June attracts headline acts from around the country and is extremely popular, as is the early three-day snow sculpturing exhibition held every winter on Navy Pier. Grant Park at the harbor hosts an annual Taste of Chicago Food Festival which, as you might expect, appeals to a wide audience.

Insider tips for Chicago travel

  • Pancho Pistolas

    Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.

  • Ping Tom Memorial Park

    Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.

  • Montrose Harbor

    Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.

  • Alta Vista Terrace

    Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.

  • Cafe Selmarie

    Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.

Chicago highlights

  • Chicago highlights
  • Navy Pier

    For a bustling carnival vibe along Lake Michigan, wander along the Navy Pier promenade and catch the spirit of Chicago. Bring the kids to the Children's Museum, Shakespeare Theatre or Stained Glass Gallery, and marvel at the incredible skyline views from the 150-foot Ferris wheel. Grab a bite to eat at Chicago institution Harry Caray's, and rest your weary feet to enjoy the free weekly fireworks.

  • Magnificent Mile

    The Mag Mile is a revered for its incredible shopping and eating scene, as well as the festivities that occur throughout the year. Lined by colorful tulips in the springtime and glittering lights during the holidays, the Mag Mile is chockablock with department stores and notable landmarks, from the Wrigley Building to Oak Street Beach. For incredible views on your Chicago travels, head to the Hancock Observatory or spend a few bucks on a cocktail in the Signature Lounge.

  • Lincoln Park Zoo

    For an easy escape without having to spend a cent on your Chicago travels, take the afternoon to meander through the menagerie at the Lincoln Park Zoo. Not only is it brimming with wildlife exhibits and beautiful historical architecture, it's totally free and open 365 days a year.

  • Cultural Chicago

    If you want to experience the cultural side of the Second City on your Chicago vacation, make a beeline for the Chicago Cultural Center where admission is free. After taking in the impressive architecture and stunning Tiffany dome, head to the Art Institute across the street to view the amazing collection of Impressionist art and the new Modern Wing. Take a stroll to the Buckingham Fountain and laze in the sun, or take in a nighttime light show.

  • Millennium Park

    Chicago has plenty of parks, but this one is worth a special mention. An impressive feat of engineering, landscaping and cultural celebration, Millennium Park is home to the iconic Cloud Gate sculpture and splashy Crown Fountain video sculpture. Enjoy a concert at Jay Pritzker Pavilion, the go-to spot for the best in outdoor entertainment.

Your trip

Hotel options

Hotel stay must be within date range of Leave and Return.

Room 1
Age categories
Ages of children at time of trip (for pricing, discounts)