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 1077 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
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Nightly rates from $125

Inn of Chicago, an Ascend Collection hotel

3 stars
3.3 / 5 217 reviews
Contemporary style, European charm in ChicagoIn the Roaring '20s, this boutique Streeterville hotel hosted celebrities and showgirls. While those times have faded, the air of glamour remains at the Inn of Chicago, an Ascend Collection hotel. For proof, just stroll the lobby, where zebra ottomans, fresh-cut orchids and metallic embossed walls create drama and urban appeal. With its central location and focus on value, the Inn of Chicago is a gem for business or leisure travelers seeking convenient access to the Magnificent Mile and its many diversions. Highlights Prime Chicago location just east of Magnificent MileFree high-speed wireless Internet accessComplimentary stay for children under 18The 22nd floor Skyline Terrace RoomsThe rooms and suites at the Inn of Chicago feel more like apartments than hotel rooms, and that’s on purpose. Back in the 1920s, the former Hotel St. Clair offered one-bedroom apartments, and the effects linger today at the Inn of Chicago. Space for entertaining, working and lounging are separate from the sleeping area. Big picture windows with skyline views, photos of Chicago, zebra upholstery and unique layouts lend to a chic city vibe. FeaturesGreat city views might well be the most valuable cache for Chicago hotels and for the Inn of Chicago, this view comes at the Skyline Terrace on the 22nd floor. The Sky Suites also provide lofty views, while a dedicated party space accommodates up to 100 guests for weddings and other social events. Transportation O’Hare International Airport (15.6 mi/25.1 km) Midway Airport (9.8 mi/15.9 km) Blue Line (Grand) (1.7mi/2.7 km) Orange Line (State/Lake) (0.5 mi/0.9 km) McCormick Place Convention Center (2.9 mi/4.6 km) Attractions The Magnificent Mile (0.1 mi/0.1 km) Water Tower Place (0.4 mi/0.6 km) Navy Pier (1 mi/1.6 km) Lake Michigan (0.2 mi/0.3 km) Millennium Park (0.7 mi/1.1 km) Business Business center work station 5 meeting rooms 5,500 square feet of function space for up to 125 guests Complimentary wireless Internet access Concierge services Policies and fees NOTE: Parking fees are as follows: $48 for self-parking and $52 for valet parking with unlimited in/out privileges.
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Nightly rates from $114

Club Quarters Central Loop

3 stars
4.1 / 5 525 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)
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Nightly rates from $80

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
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Nightly rates from $80

Kinzie Hotel (formerly the Amalfi Hotel)

4 stars
4.4 / 5 752 reviews
Occupying the first six floors of Dearborn Plaza, the newly revamped Amalfi Hotel changed its name to the Kinzie Hotel Chicago in February 2014, as a tribute to John Kinzie, one of the city's original settlers. Rounded corner suites mark the high-rise exterior out against the skyline, while the eclectic contemporary art and mismatched colors of the lobby signal a touch of the avant-garde. The hotel's cutting-edge fitness center is open around the clock, every room has an iHome docking station, and in-room dining is provided by local favorite Harry Caray's Italian Steakhouse. Ask the concierge to organize an in-room hot-stone massage as an end-of-the-day treat. Key facts210 guestroomsFitness centerIn-room diningLounge barContinental breakfast served on every floorLoungeFree Wi-Fi Dual showerheads NeighborhoodA River North hotel, the Kinzie Hotel Chicago is surrounded by a hip night scene and a wide selection of art galleries in the neighborhood. Visitors can also access The Loop financial hub if they cross south of the Chicago River, and hop on the nearby water taxi for an awe-inspiring and traffic-free way to see the Chicago skyline. Two blocks from the river and just off of Wacker Drive, the Kinzie Hotel is across the street from the Museum of Broadcast Communications, which houses radio and television memorabilia as well as interactive displays. Hints and tipsDon't miss the Manager's Reception from 5pm-8pm every night, where free cocktails and hors d'oeuvres are offered in the Double Cross Lounge.For recommended eats nearby, try Frontera Grill or Pizzeria Uno on Wabash Avenue for a slice of Chicago's famous pizza-pie.
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Nightly rates from $159
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Wed, Sep 3 - Tue, Sep 9 $195
Los Angeles Chicago Tue, Sep 9 - Tue, Sep 16 $235
Washington DC Chicago Wed, Oct 8 - Sat, Oct 11 $105
San Francisco Chicago Tue, Sep 9 - Wed, Sep 10 $265
Newark Chicago Sat, Sep 27 - Sat, Oct 4 $298
Atlanta Chicago Tue, Oct 21 - Fri, Oct 24 $125
Seattle Chicago Sat, Sep 27 - Tue, Sep 30 $299
Boston Chicago Wed, Oct 8 - Sat, Oct 18 $155
Dallas Chicago Sat, Sep 13 - Sat, Sep 20 $155
Denver Chicago Sat, Sep 27 - Sat, Oct 4 $145
Phoenix Chicago Tue, Sep 23 - Tue, Oct 7 $217
Orlando Chicago Tue, Sep 9 - Wed, Sep 10 $195
San Juan Chicago Sat, Sep 13 - Sun, Sep 21 $281
Mexico City Chicago Fri, Sep 19 - Fri, Sep 26 $356
Philadelphia Chicago Tue, Sep 16 - Mon, Sep 22 $285
San Diego Chicago Wed, Oct 15 - Sat, Oct 25 $278
Fort Lauderdale Chicago Sat, Sep 27 - Tue, Sep 30 $245
Las Vegas Chicago Thu, Sep 4 - Fri, Sep 5 $223
Guadalajara Chicago Mon, Sep 8 - Mon, Sep 15 $478
Tampa Chicago Sat, Sep 13 - Tue, Sep 23 $284
Houston Chicago Wed, Oct 1 - Sat, Oct 4 $173
Baltimore Chicago Wed, Sep 10 - Wed, Sep 17 $165
Honolulu Chicago Mon, Sep 1 - Sun, Sep 7 $742
Orange County Chicago Wed, Sep 17 - Tue, Sep 23 $291
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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.

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