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 1273 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
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Hotel only
Nightly rates from $134

Club Quarters Central Loop

3 stars
4.1 / 5 610 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)
Value Save 15% On Your Stay
Flight + Hotel
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Hotel only
Nightly rates from $109

Homewood Suites Chicago Downtown

3 stars
4.4 / 5 116 reviews
Home sweet Homewood A hot breakfast. Free Wi-Fi throughout the space. Gathering with others over wine, beer and soda. These daily conveniences might be missed while on vacation, but are customary amenities at Homewood Suites Chicago Downtown. Within walking distance of the Magnificent Mile and downtown Chicago restaurants, bars and shops, the River North Hilton property prides itself on the extras--regardless of whether the trip is for business or leisure. Highlights Complimentary daily hot breakfast buffetComplimentary Wi-Fi throughout the hotelFree nightly reception with meal, beer, wine and sodaFree grocery shopping serviceKing suites with full kitchens Rooms If these weren't hotel rooms, they might pass as city condos. Each space boasts two rooms and a full kitchen that includes a two-burner stove, microwave, dishwasher and refrigerator--ideal for a family looking to save money on dining expenses or an executive on an business trip. A wall separates the living, dining and sleeping quarters to provide maximum comfort. A palette of amber, brown and burgundy warms rooms, while several wall hangings add local flavor with images of Chicago landmarks. Guests sleep on the signature, plush Homewood Sweet Dreams mattress. LCD TV, two phone lines with voicemail and complimentary local calls are standard amenities. Features Homewood Suites Chicago Downtown provides a laundry list of bonuses that come at no extra cost to visitors. Expect a daily hot breakfast buffet, Wi-Fi throughout the space, a nightly reception with meal, beer, wine and soda, free coffee, tea or hot cider in the lobby all day, a grocery shopping service and a business center. During downtime, guests head to the indoor pool and cardio center, which are blessed with panoramic views of the Chicago skyline. Transportation O'Hare International Airport (16 miles)Midway Airport (11 miles)Closest train stops: Blue Line (Clark/Lake to O'Hare) and Orange Line (State/Lake to Midway)McCormick Place Convention Center (11 minutes) Attractions Magnificent MileMuseum of Contemporary ArtNavy PierJohn Hancock CenterTribune TowerWrigley BuildingCivic Opera House Business More than 3,000 square feet of meeting spaceFree Wi-Fi throughout the hotelBusiness center with computer and printer
Value Free hot breakfast and high speed internet access
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $134

Warwick Allerton Hotel Chicago

4 stars
4.0 / 5 642 reviews
As one of the first high-rises to grace Chicago's fashionable Michigan Avenue, the Warwick Allerton Hotel Chicago became synonymous with high style, luxurious hotel accommodations and impeccable service. Today, the hotel has kept the commitment to treat every guest like a celebrity and continues to make each stay at the Warwick Allerton Hotel Chicago as comfortable and rewarding as their predecessors did more than 80 years ago. Of all Magnificent Mile Chicago hotels, Warwick Allerton Hotel Chicago's historic Italian Renaissance style will dazzle you. The 443 guest rooms, including 84 suites, are perfect for your next Chicago meeting, banquet or wedding. The Warwick Allerton Hotel Chicago offers a variety of impressive, natural lit meeting rooms able to accommodate your group of 10 to 200. The Renaissance Ballroom located on the 23rd floor offers a stunning view of Michigan Avenue and Downtown Chicago. If you are looking for a luxury hotel in downtown Chicago, stay with us and experience our exquisite service and our great location. Welcome to the Warwick Allerton Hotel Chicago! Overnight valet parking $60 effective July 1st, 2013 A valid credit card must be presented at check-in for incidental charges.
Flight + Hotel
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Nightly rates from $107

The Talbott Hotel

4 stars
4.6 / 5 1330 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 in 2014 - 2015, the Talbott features exclusive touches like the creative Tippling Brothers cocktail menu at the Mercadito Fish Co., 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: Mercadito Fish Co. 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. Policies and feesGuests must be at least 21 years of age to check in.
Value Last Minute Deal!
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Nightly rates from $155
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Cheap Flights

Departure Arrival Travel dates Round-trip
New York Chicago Thu, May 28 - Sat, Jun 6 $177
Los Angeles Chicago Tue, May 19 - Tue, May 26 $212
Washington DC Chicago Thu, Jun 4 - Wed, Jun 10 $145
San Francisco Chicago Tue, May 12 - Wed, May 20 $244
Newark Chicago Tue, May 26 - Thu, May 28 $232
Atlanta Chicago Tue, May 19 - Tue, May 26 $97
Seattle Chicago Mon, May 25 - Thu, May 28 $245
Boston Chicago Wed, May 27 - Wed, Jun 3 $147
Dallas Chicago Sat, May 30 - Tue, Jun 2 $81
Denver Chicago Mon, Jun 1 - Tue, Jun 2 $107
Phoenix Chicago Sat, May 30 - Sat, Jun 6 $227
Orlando Chicago Tue, Jun 2 - Tue, Jun 9 $165
San Juan Chicago Thu, Jun 4 - Fri, Jun 5 $369
Mexico City Chicago Thu, Jun 4 - Thu, Jun 11 $440
Philadelphia Chicago Wed, May 27 - Sat, May 30 $90
San Diego Chicago Tue, May 19 - Tue, May 26 $237
Fort Lauderdale Chicago Tue, Jun 2 - Thu, Jun 4 $139
Las Vegas Chicago Wed, May 13 - Tue, May 19 $159
Guadalajara Chicago Wed, May 13 - Sun, May 31 $418
Tampa Chicago Tue, Jun 30 - Tue, Jul 14 $145
Houston Chicago Thu, May 28 - Wed, Jun 3 $137
Baltimore Chicago Mon, May 11 - Wed, May 13 $177
Honolulu Chicago Wed, Jun 3 - Sun, Jun 21 $823
Orange County Chicago Tue, Jun 2 - Sat, Jun 6 $356
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