Woodlawn Vacations from $730
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Your Woodlawn Vacation
From its cycling to its golfing and walking, there are tons of convincing reasons to book a vacation package to Woodlawn. When you're ready to escape the everyday, this green neighborhood is calling. Wondering what to see and do during your trip to Woodlawn? Nearby attractions such as University of Chicago, Chicago Museum of Science and Industry and Robie House are good places to begin. Expedia will help put your plans into action. Book your perfect Woodlawn vacation now.
The Latest Woodlawn Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,216, price is now $730 per person
$730
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Location was excellent. Rooms were a little smaller than I'd prefer but we got by.
Reviewed on Jun 29, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,343, price is now $840 per person
$840
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,278, price is now $837 per person
$837
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.
Reviewed on Jun 28, 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,105, price is now $746 per person
$746
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
Not for family it will work for chilling with your ex or old friends
Reviewed on Jun 29, 2026
Where to stay in Woodlawn
Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Woodlawn Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $162 total per night from Jun 30 to Jul 1
$162 total
Jun 30 - Jul 1
Total with taxes and fees
8/10 Very Good! (10,162 reviews)
"nice selection of drinks at the bar"
Reviewed on Jun 29, 2026
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $215 total per night from Jul 5 to Jul 6
$215 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (1,833 reviews)
"Staff was extremely friendly and helpful! Very clean and inviting environment!"
Reviewed on Jun 29, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $154 total per night from Jul 2 to Jul 3
$154 total
Jul 2 - Jul 3
Total with taxes and fees
8.8/10 Excellent! (2,749 reviews)
"Awesome place to stay and wine and dine"
Reviewed on Jun 28, 2026
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.
Stay near popular Woodlawn attractions
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Explore a world of travel with Expedia
- North Avenue Beach
- United Center
- Fisher Building
- Willis Tower
- Lakefront Trail
- Shops at North Bridge
- Jane Addams' Hull-House Museum
- Ohio Street Beach
- Marquette Building
- Depaul University-Loop Campus
- Driehaus Museum
- Santa Fe Building
- Film Row Cinema
- Roosevelt University
- Buckingham Fountain
- Robert W Roloson Houses
- The Salt Shed
- Downtown Chicago Vacations
- Cadillac Palace Theatre
- Chicago Vacations
- Holy Name Cathedral
- Lincoln Park Conservatory
- The Loop Vacations
- Old Colony Building
- Chicago Symphony Orchestra
- 900 North Michigan Shops
- Art Institute of Chicago
- Wrigley Building
- Rookery
- Chicago Place Mall
- Crown Fountain
- Hyde Park Vacations
- Obama's House
- Robie House
- Montrose Beach
- Carbide and Carbon Building
- Navy Pier
- Ping Tom Memorial Park
- Chicago Riverwalk
- Columbia College Chicago
- Elijah Muhammad House
- Tribune Tower
- Civic Opera House
- Grant Park
- Zhou B Art Center
- Gen. John Logan Memorial
- Canalport Riverwalk Park
- Chicago Cultural Center
- Chicago Children's Museum
- Chicago Loop Synagogue
- Water Tower Place
- Richard J. Daley Center
- Daley Plaza
- Mary Bartelme Park
- Chicago City Hall
- Lorado Taft's Midway Studios
- Symphony Center
- Picasso Statue
- Maxwell Street Market
- Skydeck Ledge
- University of Illinois Chicago
- Maggie Daley Park
- Midway Plaisance
- Marina City
- Goodman Theater
- Sr Crown Hall
- University of Chicago
- Burnham Park
- Bridgeport Art Center
- Mccormick Tribune Center
- Muddy Waters’ House
- Monadnock Building
- Wrigley Field
- South Loop Vacations
- Millennium Park
- American Police Center & Museum
- Auditorium Building and Theatre
- Chicago Architecture Foundation
- 311 S Wacker Dr
- Chicago Board of Trade Building
- South Commons Vacations
- Dusable Museum of African-American History
- Unity Temple
- Cna Center
- Chinatown Vacations
- Michigan Avenue
- Pontiac Building
- Lincoln Park Zoo
- Grace Abbott Homes Vacations
- Cibc Theatre
- Marshall Field Building
- Chicago Museum Campus Vacations
- Michigan Avenue Bridge
- 333 West Wacker Drive
- Magnificent Mile Vacations
- Merchandise Mart
- Griffin Museum of Science and Industry
- Chase Tower
- Ida B Wells House
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.